{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,28]],"date-time":"2026-09-28T09:56:03Z","timestamp":1790589363618,"version":"4.1.0"},"reference-count":88,"publisher":"American Chemical Society (ACS)","issue":"9","license":[{"start":{"date-parts":[[2017,12,29]],"date-time":"2017-12-29T00:00:00Z","timestamp":1514505600000},"content-version":"vor","delay-in-days":1213,"URL":"https:\/\/pubs.acs.org\/page\/policy\/authorchoice_termsofuse.html"}],"funder":[{"DOI":"10.13039\/na","name":"Foundation for Development of Diagnostics and Therapy, Poland","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/na","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2014,9,22]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Three anhydrous methylxanthines: caffeine (1,3,7-trimethylxanthine; 1,3,7-trimethyl-1H-purine-2,6-(3H,7H)-dione) and its two metabolites theophylline (1,3-dimethylxanthine; 1,3-dimethyl-7H-purine-2,6-dione) and theobromine (3,7-dimethyl-xanthine; 3,7-dimethyl-7H-purine-2,6-dione), which reveal multifaceted therapeutic potential, have been studied experimentally in solid state by 1H\u201314N NMR-NQR (nuclear magnetic resonance\u2013nuclear quadrupole resonance) double resonance (NQDR). For each compound the complete NQR spectrum consisting of 12 lines was recorded. The multiplicity of NQR lines indicates the presence of a stable \u03b2 form of anhydrous caffeine at 233 K and stable form II of anhydrous theobromine at 213 K. The assignment of signals detected in NQR experiment to particular nitrogen atoms was made on the basis of quantum chemistry calculations performed for monomer, cluster, and solid at the DFT\/GGA\/BLYP\/DPD level. The shifts due to crystal packing interactions were evaluated, and the multiplets detected by NQR were assigned to N(9) in theobromine and N(1) and N(9) in caffeine. The ordering theobromine &amp;gt; theophylline &amp;gt; caffeine site and theophylline &amp;lt; theobromine &amp;lt; caffeine according to increasing electric field gradient (EFG) at the N(1) and N(7) sites, respectively, reflects the changes in biological activity profile of compounds from the methylxanthines series (different pharmacological effects). This difference is elucidated on the basis of the ability to form intra- and intermolecular interactions (hydrogen bonds and \u03c0\u00b7\u00b7\u00b7\u03c0 stacking interactions). The introduction of methyl groups to xanthine restricts the ability of nitrogen atoms to participate in strong hydrogen bonds; as a result, the dominating effect shifts from hydrogen bond (theobromine) to \u03c0\u00b7\u00b7\u00b7\u03c0 stacking (caffeine). Substantial differences in the intermolecular interactions in stable forms of methylxanthines differing in methylation (site or number) were analyzed within the Hirshfeld surface-based approach. The analysis of local environment of the nitrogen nucleus permitted drawing some conclusions on the nature of the interactions required for effective processes of recognition and binding of a given methylxanthine to A1\u2013A2A receptor (target for caffeine in the brain). Although the interactions responsible for linking neighboring methylxanthines molecules in crystals and methylxanthines with targets in the human organism can differ significantly, the knowledge of the topology of interactions provides reliable preliminary information about the nature of this binding.<\/jats:p>","DOI":"10.1021\/ci5004224","type":"journal-article","created":{"date-parts":[[2014,9,3]],"date-time":"2014-09-03T15:51:58Z","timestamp":1409759518000},"page":"2570-2584","source":"Crossref","is-referenced-by-count":26,"title":["Topology\nof the Interactions Pattern in Pharmaceutically\nRelevant Polymorphs of Methylxanthines (Caffeine, Theobromine, and\nTheophiline): Combined Experimental (1H\u201314N Nuclear Quadrupole Double Resonance) and Computational (DFT and\nHirshfeld-Based) Study"],"prefix":"10.1021","volume":"54","author":[{"given":"Jolanta Natalia","family":"Latosin\u0301ska","sequence":"first","affiliation":[{"name":"Adam Mickiewicz University , , Umultowska 85 , ,","place":["Poznan\u0301, Poland, 61-614"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Magdalena","family":"Latosin\u0301ska","sequence":"additional","affiliation":[{"name":"Adam Mickiewicz University , , Umultowska 85 , ,","place":["Poznan\u0301, Poland, 61-614"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Grzegorz A.","family":"Olejniczak","sequence":"additional","affiliation":[{"name":"Adam Mickiewicz University , , Umultowska 85 , ,","place":["Poznan\u0301, Poland, 61-614"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Janez","family":"Seliger","sequence":"additional","affiliation":[{"name":"\u201cJozef Stefan\u201d Institute , Jamova 39 , ,","place":["Ljubljana, Slovenia, 1000"]},{"name":"University of Ljubljana , , Jadranska 19 , ,","place":["Ljubljana, Slovenia, 1000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Veselko","family":"Z\u030cagar","sequence":"additional","affiliation":[{"name":"\u201cJozef Stefan\u201d Institute , Jamova 39 , ,","place":["Ljubljana, Slovenia, 1000"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2014,9,3]]},"reference":[{"issue":"8","key":"2026092805064230000_cit1","doi-asserted-by":"crossref","first-page":"2575","DOI":"10.1016\/0031-9422(92)83590-U","article-title":"Purine\nand Purine Alkaloid Metabolism\nin Camellia and Coffea Plants","volume":"31","author":"Suzuki","year":"1992","journal-title":"Phytochemistry"},{"issue":"2","key":"2026092805064230000_cit2","doi-asserted-by":"crossref","first-page":"121","DOI":"10.1016\/0378-8741(87)90084-5","article-title":"Natural Constituents\nof Ilex Species","volume":"20","author":"Alikaridis","year":"1987","journal-title":"J. Ethnopharmacol."},{"issue":"1","key":"2026092805064230000_cit3","doi-asserted-by":"crossref","first-page":"35","DOI":"10.1016\/0308-8146(91)90017-I","article-title":"Phenols\nand Caffeine in Wet-Processed Coffee Beans\nand Coffee Pulp","volume":"40","author":"Clifford","year":"1991","journal-title":"Food Chem."},{"issue":"3","key":"2026092805064230000_cit4","doi-asserted-by":"crossref","first-page":"185","DOI":"10.1016\/S0896-8446(96)90031-5","article-title":"Supercritical Carbon\nDioxide Extraction of caffeine from guarana\u0301","volume":"9","author":"Mehr","year":"1996","journal-title":"J. Supercrit. Fluids"},{"issue":"4","key":"2026092805064230000_cit5","doi-asserted-by":"crossref","first-page":"423","DOI":"10.1007\/BF02523913","article-title":"A New Industrial Process for Extracting Cocoa Butter\nand Xanthines with Supercritical Carbon Dioxide","volume":"73","author":"Li","year":"1996","journal-title":"J. Am. Oil Chem. Soc."},{"issue":"4671","key":"2026092805064230000_cit6","doi-asserted-by":"crossref","first-page":"184","DOI":"10.1126\/science.6207592","article-title":"Caffeine and\nRelated Methylxanthines: Possible Naturally Occurring Pesticides","volume":"226","author":"Nathanson","year":"1984","journal-title":"Science"},{"issue":"6892","key":"2026092805064230000_cit7","doi-asserted-by":"crossref","first-page":"915","DOI":"10.1038\/417915a","article-title":"Caffeine as a Repellent for Slugs\nand Snails","volume":"417","author":"Hollingsworth","year":"2002","journal-title":"Nature"},{"issue":"3","key":"2026092805064230000_cit8","doi-asserted-by":"crossref","first-page":"109","DOI":"10.1007\/BF00269330","article-title":"High Production\nof Caffeine and Related\nEnzyme Activities in Callus Cultures of Coffea Arabica L","volume":"2","author":"Waller","year":"1983","journal-title":"Plant Cell Rep."},{"issue":"6124","key":"2026092805064230000_cit9","doi-asserted-by":"crossref","first-page":"1202","DOI":"10.1126\/science.1228806","article-title":"Caffeine\nin Floral Nectar Enhances a Pollinator\u2019s Memory of Reward","volume":"339","author":"Wright","year":"2013","journal-title":"Science"},{"issue":"11","key":"2026092805064230000_cit10","doi-asserted-by":"crossref","first-page":"1064","DOI":"10.1001\/2013.jamaoto.342","article-title":"Intranasal Theophylline Treatment\nof Hyposmia and Hypogeusia: A Pilot Study","volume":"138","author":"Henkin","year":"2012","journal-title":"Arch.\nOtolaryngol. Head Neck Surg."},{"key":"2026092805064230000_cit11","first-page":"382","volume-title":"Caffeine and Activation\nTheory: Effects on Health and Behavior","author":"Smith","year":"2007"},{"issue":"15","key":"2026092805064230000_cit12","doi-asserted-by":"crossref","first-page":"1026","DOI":"10.1056\/NEJM199010113231504","article-title":"Coffee, Caffeine, and Cardiovascular Disease in Men","volume":"323","author":"Grobbee","year":"1990","journal-title":"N. Engl. J. Med."},{"issue":"2","key":"2026092805064230000_cit13","doi-asserted-by":"crossref","first-page":"647","DOI":"10.1161\/01.HYP.33.2.647","article-title":"The Effect of Chronic\nCoffee Drinking on Blood Pressure: A Meta-Analysis of Controlled Clinical\nTrials","volume":"33","author":"Jee","year":"1999","journal-title":"Hypertension"},{"issue":"1","key":"2026092805064230000_cit14","doi-asserted-by":"crossref","first-page":"54","DOI":"10.1016\/0002-9343(84)90435-2","article-title":"Caffeine and Hypertension","volume":"77","author":"Robertson","year":"1984","journal-title":"Am. J. Med."},{"issue":"11","key":"2026092805064230000_cit15","doi-asserted-by":"crossref","first-page":"831","DOI":"10.1038\/sj.ejcn.1600899","article-title":"Coffee, Caffeine\nand Blood Pressure: a Critical Review","volume":"53","author":"Nurminen","year":"1999","journal-title":"Eur.\nJ. Clin. Nutr."},{"issue":"20","key":"2026092805064230000_cit16","doi-asserted-by":"crossref","first-page":"2674","DOI":"10.1001\/jama.283.20.2674","article-title":"Association of Coffee\nand Caffeine Intake with the Risk of Parkinson Disease","volume":"283","author":"Ross","year":"2000","journal-title":"J. Am. Med. Assoc."},{"issue":"7","key":"2026092805064230000_cit17","doi-asserted-by":"crossref","first-page":"651","DOI":"10.1212\/WNL.0b013e318263570d","article-title":"Caffeine for Treatment\nof Parkinson Disease: A Randomized Controlled Trial","volume":"79","author":"Postuma","year":"2012","journal-title":"Neurology"},{"issue":"5","key":"2026092805064230000_cit18","doi-asserted-by":"crossref","first-page":"756","DOI":"10.1111\/j.1468-1331.2011.03353.x","article-title":"Coffee,\nADORA2A, and CYP1A2: the Caffeine Connection in Parkinson\u2019s\ndisease","volume":"18","author":"Popat","year":"2011","journal-title":"Eur. J. Neurol."},{"issue":"Suppl 1","key":"2026092805064230000_cit19","doi-asserted-by":"crossref","first-page":"S167","DOI":"10.3233\/JAD-2010-1404","article-title":"Caffeine as\na Protective Factor in Dementia and Alzheimer\u2019s\nDisease","volume":"20","author":"Eskelinen","year":"2010","journal-title":"J. Alzheimer\u2019s Dis."},{"issue":"4","key":"2026092805064230000_cit20","doi-asserted-by":"crossref","first-page":"377","DOI":"10.1046\/j.1468-1331.2002.00421.x","article-title":"Does Caffeine Intake\nProtect from Alzheimer\u2019s\ndisease?","volume":"9","author":"Maia","year":"2002","journal-title":"Eur. J. Neurol."},{"issue":"Suppl 1","key":"2026092805064230000_cit21","doi-asserted-by":"crossref","first-page":"S143","DOI":"10.3233\/JAD-2010-091228","article-title":"Caffeine,\nDiabetes, Cognition, and Dementia","volume":"20","author":"Biessels","year":"2010","journal-title":"J. Alzheimer\u2019s\nDis."},{"issue":"06","key":"2026092805064230000_cit22","doi-asserted-by":"crossref","first-page":"773","DOI":"10.1079\/BJN20051370","article-title":"Is Coffee a Functional Food?","volume":"93","author":"Do\u0301rea","year":"2005","journal-title":"Br. J. Nutr."},{"issue":"200","key":"2026092805064230000_cit23","doi-asserted-by":"crossref","first-page":"201","DOI":"10.1007\/978-3-642-13443-2_7","article-title":"Theobromine\nand the Pharmacology of Cocoa","author":"Smit","year":"2011","journal-title":"Handb. Exp. Pharmacol"},{"issue":"6","key":"2026092805064230000_cit24","doi-asserted-by":"crossref","first-page":"1588","DOI":"10.1016\/j.jaci.2013.11.017","article-title":"Theophylline\nInhibits the Cough Reflex\nThrough a Novel Mechanism of Action","volume":"133","author":"Dubuis","year":"2014","journal-title":"J. Allergy\nClin. Immunol."},{"key":"2026092805064230000_cit25","doi-asserted-by":"crossref","first-page":"476","DOI":"10.1016\/j.neuropharm.2012.11.029","article-title":"Psychostimulant Pharmacological\nProfile of Paraxanthine, the Main Metabolite of Caffeine in Humans","volume":"67","author":"Orru","year":"2013","journal-title":"Neuropharmacology"},{"issue":"6","key":"2026092805064230000_cit26","doi-asserted-by":"crossref","first-page":"2103","DOI":"10.1073\/pnas.94.6.2103","article-title":"Altered DNA Methylation and Genome Instability: a New\nPathway to Cancer?","volume":"94","author":"Jones","year":"1997","journal-title":"Proc. Natl. Acad. Sci. U.\nS. A."},{"issue":"2","key":"2026092805064230000_cit27","doi-asserted-by":"crossref","first-page":"121","DOI":"10.1016\/j.canlet.2008.08.022","article-title":"Coffee Consumption\nand the Risk of Cancer: An Overview","volume":"277","author":"Nkondjock","year":"2009","journal-title":"Cancer\nLett."},{"issue":"5","key":"2026092805064230000_cit28","doi-asserted-by":"crossref","first-page":"915","DOI":"10.1002\/mnfr.201300526","article-title":"Coffee and Cancer Risk, Epidemiological\nEvidence, and Molecular Mechanisms","volume":"58","author":"B\u00f8hn","year":"2014","journal-title":"Mol. Nutr.\nFood Res."},{"issue":"13","key":"2026092805064230000_cit29","doi-asserted-by":"crossref","first-page":"3282","DOI":"10.1158\/0008-5472.CAN-11-3511","article-title":"Increased Caffeine Intake is Associated\nWith Reduced Risk of Basal Cell Carcinoma of the Skin","volume":"72","author":"Song","year":"2012","journal-title":"Cancer Res."},{"issue":"2","key":"2026092805064230000_cit30","doi-asserted-by":"crossref","first-page":"346","DOI":"10.1017\/S1368980012002601","article-title":"Coffee Consumption\nand Risk of Colorectal Cancer: A Meta-Analysis of Observational Studies","volume":"16","author":"Li","year":"2013","journal-title":"Public Health Nutr."},{"issue":"7","key":"2026092805064230000_cit31","doi-asserted-by":"crossref","first-page":"1805","DOI":"10.1038\/jid.2008.435","article-title":"ATR-Chk1 Pathway Inhibition Promotes Apoptosis after\nUV Treatment in Primary Human Keratinocytes: Potential Basis for the\nUV Protective Effects of Caffeine","volume":"129","author":"Heffernan","year":"2009","journal-title":"J. Invest.\nDermatol."},{"issue":"7","key":"2026092805064230000_cit32","doi-asserted-by":"crossref","first-page":"1611","DOI":"10.1038\/jid.2009.99","article-title":"UVB and Caffeine: Inhibiting the DNA Damage Response\nto Protect Against the Adverse Effects of UVB","volume":"129","author":"Kerzendorfer","year":"2009","journal-title":"J. Invest. Dermatol."},{"issue":"19","key":"2026092805064230000_cit33","doi-asserted-by":"crossref","first-page":"12455","DOI":"10.1073\/pnas.182429899","article-title":"Topical\nApplications\nof Caffeine or (\u2212)-epigallocatechin gallate (EGCG) Inhibit\nCarcinogenesis and Selectively Increase Apoptosis in UVB-induced Skin\nTumors in Mice","volume":"99","author":"Lu","year":"2002","journal-title":"Proc. Natl. Acad. Sci. U. S.\nA."},{"issue":"4","key":"2026092805064230000_cit34","doi-asserted-by":"crossref","first-page":"325","DOI":"10.2174\/138920108785161497","article-title":"Modulation of Cellular Response to Anticancer Treatment\nby Caffeine: Inhibition of Cell Cycle Checkpoints, DNA Repair and\nMore","volume":"9","author":"Sabisz","year":"2008","journal-title":"Curr. Pharm. Biotechnol."},{"issue":"5","key":"2026092805064230000_cit35","doi-asserted-by":"crossref","first-page":"375","DOI":"10.1016\/0278-6915(86)90201-2","article-title":"Evaluation\nof the Perinatal, Postnatal and Teratogenic Effects of Cocoa Powder\nand Theobromine in Sprague-Dawley\/CD rats","volume":"24","author":"Tarka","year":"1986","journal-title":"Food\nChem. Toxicol."},{"issue":"1","key":"2026092805064230000_cit36","doi-asserted-by":"crossref","first-page":"7","DOI":"10.1016\/0278-6915(91)90057-E","article-title":"Chronic Toxicity\/Carcinogenicity Studies of Cocoa Powder\nin Rats","volume":"29","author":"Tarka","year":"1991","journal-title":"Food Chem. Toxicol."},{"issue":"10","key":"2026092805064230000_cit37","doi-asserted-by":"crossref","first-page":"795","DOI":"10.1016\/0278-6915(87)90236-5","article-title":"Genotoxicity\nand Carcinogenicity Assessments of Caffeine and Theobromine","volume":"25","author":"Grice","year":"1987","journal-title":"Food Chem. Toxicol."},{"key":"2026092805064230000_cit38","unstructured":"Lee, H. J.; Lee, K. W.; Kang, K. S.; Kim, D. Y.; Park, H. H.; Lee, M. J.; Kim, H. S.; Kwon, I. B.\n          Theobromine\nwith an anti-carcinogenic activity, Lotte. Confectionery Co., Ltd.(Seoul,\nKR), US\npatent 6693104, 2004."},{"key":"2026092805064230000_cit39","doi-asserted-by":"crossref","first-page":"35","DOI":"10.5772\/52507","article-title":"Anticancer\nDrug Discovery - From Serendipity to Rational Design","volume-title":"Drug Discovery","author":"Latosin\u0301ska","year":"2013"},{"issue":"1","key":"2026092805064230000_cit40","doi-asserted-by":"crossref","first-page":"141","DOI":"10.1016\/j.nurt.2008.10.035","article-title":"Dual-target-Directed Frugs that Block Monoamine Oxidase\nB and Adenosine A(2A) Receptors for Parkinson\u2019s Disease","volume":"6","author":"Petzer","year":"2009","journal-title":"Neurotherapeutics JASEN"},{"key":"2026092805064230000_cit41","doi-asserted-by":"crossref","first-page":"267","DOI":"10.1007\/978-3-642-13443-2_10","article-title":"Impacts of Methylxanthines and Adenosine Receptors\non Neurodegeneration: Human and Experimental Studies","volume-title":"Methylxanthines","author":"Chen","year":"2011"},{"issue":"5","key":"2026092805064230000_cit42","doi-asserted-by":"crossref","first-page":"816","DOI":"10.1016\/j.physbeh.2011.07.027","article-title":"Differential Contributions of Theobromine\nand Caffeine on Mood, Psychomotor Performance and Blood Pressure","volume":"104","author":"Mitchell","year":"2011","journal-title":"Physiol. Behav."},{"issue":"1\u20132","key":"2026092805064230000_cit43","doi-asserted-by":"crossref","first-page":"187","DOI":"10.1016\/S0378-5173(98)00257-9","article-title":"Effects of Surface Active Characteristics and Solid\nState Forms on the pH Solubility Profiles of Drug\u2013Salt Systems","volume":"174","author":"Ledwidge","year":"1998","journal-title":"Int. J. Pharm."},{"issue":"24","key":"2026092805064230000_cit44","doi-asserted-by":"crossref","first-page":"7507","DOI":"10.1016\/j.bmc.2011.10.036","article-title":"Thio- and Aminocaffeine\nAnalogues\nas Inhibitors of Human Monoamine Oxidase","volume":"19","author":"Booysen","year":"2011","journal-title":"Bioorg.\nMed. Chem."},{"issue":"5","key":"2026092805064230000_cit45","doi-asserted-by":"crossref","first-page":"1445","DOI":"10.1021\/jp210322p","article-title":"Nature of Isomerism of Solid Isothiourea\nSalts, Inhibitors of Nitric Oxide Synthases, as Studied by 1H-14N Nuclear Quadrupole Double Resonance, X-Ray, and\nDensity Functional Theory\/Quantum Theory of Atoms in Molecules","volume":"116","author":"Latosin\u0301ska","year":"2012","journal-title":"J. Phys. Chem. A"},{"issue":"30","key":"2026092805064230000_cit46","doi-asserted-by":"crossref","first-page":"8793","DOI":"10.1021\/jp302659k","article-title":"Electron\nConfiguration and Hydrogen-Bonding Pattern in Several Thymine and\nUracil Analogues Studied by 1H\u2013 14N NQDR\nand DFT\/QTAIM","volume":"116","author":"Seliger","year":"2012","journal-title":"J. Phys. Chem. B"},{"issue":"4\u20136","key":"2026092805064230000_cit47","doi-asserted-by":"crossref","first-page":"293","DOI":"10.1016\/j.cplett.2009.06.038","article-title":"Electron Density Distribution in Cladribine (2-chloro-2\u2032-deoxyadenosine)\n\u2013 A Drug Against Leukemia and Multiple Sclerosis \u2013 Studied\nby Multinuclear NQR Spectroscopy and DFT Calculations","volume":"476","author":"Latosin\u0301ska","year":"2009","journal-title":"Chem. Phys. Lett."},{"issue":"16","key":"2026092805064230000_cit48","doi-asserted-by":"crossref","first-page":"2153","DOI":"10.1007\/s00018-007-7051-9","article-title":"Caffeine\nAnalogs: Biomedical Impact","volume":"64","author":"Daly","year":"2007","journal-title":"Cell. Mol. Life\nSci."},{"issue":"2","key":"2026092805064230000_cit49","doi-asserted-by":"crossref","first-page":"189","DOI":"10.1007\/BF01320180","article-title":"Proton-14N Double Resonance Study of the Structural Phase Transitions in the\nPerovskite Type Layer Compound (CH3NH3)2CdCl4","volume":"25","author":"Seliger","year":"1976","journal-title":"Z. Phys. B: Condens.\nMatter"},{"issue":"1","key":"2026092805064230000_cit50","doi-asserted-by":"crossref","first-page":"54","DOI":"10.1016\/j.jmr.2008.04.020","article-title":"Measurement of the 14N Nuclear Quadrupole\nResonance Rrequencies by the Solid Effect","volume":"193","author":"Seliger","year":"2008","journal-title":"J.\nMagn. Reson."},{"issue":"4","key":"2026092805064230000_cit51","doi-asserted-by":"crossref","first-page":"469","DOI":"10.1007\/s00723-011-0303-8","article-title":"New Methods for Detection of 14N NQR Frequencies","volume":"43","author":"Seliger","year":"2012","journal-title":"Appl. Magn. Reson."},{"issue":"12","key":"2026092805064230000_cit52","doi-asserted-by":"crossref","first-page":"5087","DOI":"10.1063\/1.1678193","article-title":"14N NQR Spectroscopy of Some Amino Acids and Nucleic Bases via Double\nResonance in the Laboratory Frame","volume":"57","author":"Blinc","year":"1972","journal-title":"J. Chem.\nPhys."},{"issue":"2","key":"2026092805064230000_cit53","doi-asserted-by":"crossref","first-page":"175","DOI":"10.1016\/j.jmr.2008.06.021","article-title":"Sensitivity of Nuclear-Quadrupole Double-Resonance Detection of Half-Integer\nSpin Nuclei","volume":"194","author":"Seliger","year":"2008","journal-title":"J. Magn. Reson."},{"issue":"2","key":"2026092805064230000_cit54","doi-asserted-by":"crossref","first-page":"214","DOI":"10.1006\/jmra.1994.1027","article-title":"A New Highly\nSensitive 1H-14N Nuclear-Quandrupole Double-Resonance\nTechnique","volume":"106","author":"Seliger","year":"1994","journal-title":"J. Magn. Reson. A"},{"key":"2026092805064230000_cit55","doi-asserted-by":"crossref","first-page":"31","DOI":"10.1515\/zna-1994-1-208","article-title":"1H-14N Nuclear\nQuadrupole Double Resonance with Multiple Frequency Sweeps","volume":"49a","author":"Seliger","year":"1994","journal-title":"Z. Natuforsch."},{"key":"2026092805064230000_cit56","volume-title":"Gaussian 09 Revision D.01","author":"Frisch","year":"2009"},{"issue":"1","key":"2026092805064230000_cit57","doi-asserted-by":"crossref","first-page":"508","DOI":"10.1063\/1.458452","article-title":"An All-electron\nNumerical Method for Solving the Local Density Functional for Polyatomic\nMolecules","volume":"92","author":"Delley","year":"1990","journal-title":"J. Chem. Phys."},{"issue":"18","key":"2026092805064230000_cit58","doi-asserted-by":"crossref","first-page":"7756","DOI":"10.1063\/1.1316015","article-title":"From Molecules\nto Solids with the DMol3 Approach","volume":"113","author":"Delley","year":"2000","journal-title":"J. Chem. Phys."},{"issue":"2","key":"2026092805064230000_cit59","doi-asserted-by":"crossref","first-page":"1372","DOI":"10.1063\/1.464304","article-title":"A New Mixing\nof Hartree\u2013Fock and Local Density-Functional Theories","volume":"98","author":"Becke","year":"1993","journal-title":"J. Chem. Phys."},{"issue":"2","key":"2026092805064230000_cit60","doi-asserted-by":"crossref","first-page":"785","DOI":"10.1103\/PhysRevB.37.785","article-title":"Development of the Colle-Salvetti\nCorrelation-Energy Formula Into a Functional of the Electron Density","volume":"37","author":"Lee","year":"1988","journal-title":"Phys. Rev. B"},{"issue":"16\u201318","key":"2026092805064230000_cit61","doi-asserted-by":"crossref","first-page":"1965","DOI":"10.1080\/00268970802018367","article-title":"Year-2008\nNuclear Quadrupole Moments","volume":"106","author":"Pyykko\u0308","year":"2008","journal-title":"Mol. Phys."},{"issue":"66","key":"2026092805064230000_cit62","doi-asserted-by":"crossref","first-page":"378","DOI":"10.1039\/B203191B","article-title":"Fingerprinting intermolecular interactions in molecular\ncrystalsBased on the presentation given at CrystEngComm Discussion,\n29th June-1st July 2002, Bristol, UK","volume":"4","author":"Spackman","year":"2002","journal-title":"CrystEngComm"},{"issue":"1","key":"2026092805064230000_cit63","doi-asserted-by":"crossref","first-page":"19","DOI":"10.1039\/B818330A","article-title":"Hirshfeld\nSurface Analysis","volume":"11","author":"Spackman","year":"2009","journal-title":"CrystEngComm"},{"issue":"1","key":"2026092805064230000_cit64","doi-asserted-by":"crossref","first-page":"563","DOI":"10.1021\/jp9075492","article-title":"Structural\nStudy of Selected Polyhalogenated Benzimidazoles (Protein Kinase CK2\nInhibitors) by Nuclear Quadrupole Double Resonance, X-ray, and Density\nFunctional Theory","volume":"114","author":"Latosin\u0301ska","year":"2010","journal-title":"J.Phys. Chem. A"},{"key":"2026092805064230000_cit65","doi-asserted-by":"publisher","DOI":"10.1021\/jp504871y","article-title":"An Insight Into Prototropism and Supramolecular Motifs\nin Solid-State Structure of Allopurinol, Hypoxanthine, Xanthine and\nUric Acid. A 1H-14N NQDR Spectroscopy and Hybrid DFT\/QTAIM\nand Hirshfeld Surface-Based Study","author":"Latosin\u0301ska","year":"2014","journal-title":"J. Phys.\nChem. B"},{"issue":"3","key":"2026092805064230000_cit66","doi-asserted-by":"crossref","first-page":"284","DOI":"10.1002\/qua.10451","article-title":"NQR parameters:\nElectric Field Gradient Tensor and Asymmetry Parameter Studied in\nTerms of Density Functional Theory","volume":"91","author":"Latosin\u0301ska","year":"2003","journal-title":"Int. J.\nQuantum Chem."},{"issue":"10","key":"2026092805064230000_cit67","doi-asserted-by":"crossref","first-page":"2908","DOI":"10.1002\/chem.200600973","article-title":"The Crystal Structure of Anhydrous Beta-Caffeine as\nDetermined from X-ray Powder-Diffraction Data","volume":"13","author":"Lehmann","year":"2007","journal-title":"Chemistry"},{"issue":"6","key":"2026092805064230000_cit68","doi-asserted-by":"crossref","first-page":"777","DOI":"10.1107\/S0108270197001960","article-title":"Anhydrous\nTheophylline","volume":"53","author":"Ebisuzaki","year":"1997","journal-title":"Acta Crystallogr. Sect. C Cryst.\nStruct. Commun."},{"issue":"12","key":"2026092805064230000_cit69","doi-asserted-by":"crossref","first-page":"1980","DOI":"10.1107\/S0108270198009469","article-title":"Methylxanthines. II. Anhydrous Theobromine","volume":"54","author":"Ford","year":"1998","journal-title":"Acta Crystallogr. Sect. C Cryst. Struct. Commun."},{"issue":"10","key":"2026092805064230000_cit70","doi-asserted-by":"crossref","first-page":"1985","DOI":"10.1039\/a702041d","article-title":"Metamorphosis\nof Caffeine Hydrate and Anhydrous Caffeine","author":"Edwards","year":"1997","journal-title":"J. Chem. Soc. Perkin Trans. 2"},{"issue":"6","key":"2026092805064230000_cit71","doi-asserted-by":"crossref","first-page":"468","DOI":"10.1252\/jcej.40.468","article-title":"Kinetics of Solid State Polymorphic Transition of Caffeine","volume":"40","author":"Matsuo","year":"2007","journal-title":"J. Chem. Eng. Jpn."},{"key":"2026092805064230000_cit72","doi-asserted-by":"crossref","first-page":"329","DOI":"10.1107\/S010876810500546X","article-title":"Ab initio Structure Determination\nof the High-temperature Phase of Anhydrous Caffeine by X-ray Powder\nDiffraction","volume":"61","author":"Derollez","year":"2005","journal-title":"Acta Crystallogr. Sect. B, Struct.\nSci."},{"issue":"8","key":"2026092805064230000_cit73","doi-asserted-by":"crossref","first-page":"1406","DOI":"10.1021\/cg070291o","article-title":"The Structure\nof Two Anhydrous Polymorphs of Caffeine from Single-Crystal Diffraction\nand Ultrahigh-Field Solid-State 13C NMR Spectroscopy","volume":"7","author":"Enright","year":"2007","journal-title":"Cryst. Growth Des."},{"issue":"20","key":"2026092805064230000_cit74","doi-asserted-by":"crossref","first-page":"204514","DOI":"10.1063\/1.3144878","article-title":"Thermal Behavior of Disordered Phase\nof Caffeine Molecular\nCrystal: Insights from Monte Carlo Simulation Studies","volume":"130","author":"Murugan","year":"2009","journal-title":"J. Chem. Phys."},{"issue":"8","key":"2026092805064230000_cit75","doi-asserted-by":"crossref","first-page":"3600","DOI":"10.1021\/cg2005612","article-title":"Form II Caffeine:\nA Case Study for Confirming and Predicting Disorder in Organic Crystals","volume":"11","author":"Habgood","year":"2011","journal-title":"Cryst. Growth Des."},{"issue":"2","key":"2026092805064230000_cit76","doi-asserted-by":"crossref","first-page":"411","DOI":"10.1021\/cg060299i","article-title":"Solid-State Polymorphic Transition\nof Theophylline\nAnhydrate and Humidity Effect","volume":"7","author":"Matsuo","year":"2007","journal-title":"Cryst. Growth\nDes."},{"issue":"3","key":"2026092805064230000_cit77","doi-asserted-by":"crossref","first-page":"253","DOI":"10.1252\/jcej.09we211","article-title":"Surface Phenomena and Mechanism of Polymorphic Transition\nin Theophylline","volume":"43","author":"Kishi","year":"2010","journal-title":"J. Chem. Eng. Jpn."},{"issue":"7","key":"2026092805064230000_cit78","doi-asserted-by":"crossref","first-page":"251","DOI":"10.1002\/ardp.19432810703","article-title":"U\u0308ber\ndie Schmelzpunkte des Pantokains, Bromurals und Theophyllins","volume":"281","author":"Doser","year":"1943","journal-title":"Archiv der Pharmazie"},{"issue":"3\u20134","key":"2026092805064230000_cit79","doi-asserted-by":"crossref","first-page":"273","DOI":"10.1007\/BF01197380","article-title":"On the Polymorphism of Pharmaceuticals and Other Molecular\nCrystals. II","volume":"72","author":"Burger","year":"1979","journal-title":"Mikrochim. Acta"},{"issue":"11","key":"2026092805064230000_cit80","doi-asserted-by":"crossref","first-page":"1256","DOI":"10.1021\/js9701418","article-title":"Polymorphism\nin Anhydrous Theophylline-Implications\non the Dissolution Rate of Theophylline Tablets","volume":"86","author":"Phadnis","year":"1997","journal-title":"J. Pharm. Sci."},{"issue":"2","key":"2026092805064230000_cit81","doi-asserted-by":"crossref","first-page":"493","DOI":"10.1248\/cpb.37.493","article-title":"Thermochemical Study of Theophylline\nand its Hydrate","volume":"37","author":"Suzuki","year":"1989","journal-title":"Chem. Pharm. Bull."},{"issue":"12","key":"2026092805064230000_cit82","doi-asserted-by":"crossref","first-page":"o496","DOI":"10.1107\/S010827011104786X","article-title":"Polymorphs\nof Anhydrous Theophylline: Stable Form IV Consists of Dimer Pairs\nand Metastable Form I Consists of Hydrogen-Bonded Chains","volume":"67","author":"Khamar","year":"2011","journal-title":"Acta Crystallogr. Sect. C Cryst. Struct. Commun."},{"issue":"9","key":"2026092805064230000_cit83","doi-asserted-by":"crossref","first-page":"3879","DOI":"10.1021\/cg100165t","article-title":"Solid State Forms\nof Theophylline: Presenting a New Anhydrous Polymorph","volume":"10","author":"Seton","year":"2010","journal-title":"Cryst. Growth Des."},{"key":"2026092805064230000_cit84","doi-asserted-by":"crossref","first-page":"o496","DOI":"10.1107\/S010827011104786X","article-title":"Polymorphs\nof Anhydrous Theophylline: Stable Form IV Consists of Dimer Pairs\nand Metastable Form I Consists of Hydrogen-Bonded Chains","volume":"67","author":"Khamar","year":"2011","journal-title":"Acta Crystallogr. Sect. C Cryst. Struct. Commun."},{"issue":"6","key":"2026092805064230000_cit85a","doi-asserted-by":"crossref","first-page":"464","DOI":"10.1107\/S0021889881009783","article-title":"Crystal\nData for Anhydrous Theophylline","volume":"14","author":"Naqvi","year":"1981","journal-title":"J. Appl. Crystallogr."},{"issue":"3","key":"2026092805064230000_cit85b","doi-asserted-by":"crossref","first-page":"1395","DOI":"10.1021\/cg201499s","article-title":"New Insights into\nan Old Molecule: Interaction Energies of Theophylline Crystal Forms","volume":"12","author":"Fucke","year":"2012","journal-title":"Crys. Growth Des."},{"issue":"3","key":"2026092805064230000_cit86","doi-asserted-by":"crossref","first-page":"613","DOI":"10.1081\/NCN-120030719","article-title":"QSAR Analysis for ADA Upon Interaction With a Series\nof Adenine Derivatives as Inhibitors","volume":"23","author":"Moosavi-Movahedi","year":"2004","journal-title":"Nucleos.\nNucleot. Nucl."},{"issue":"1","key":"2026092805064230000_cit87","first-page":"43","article-title":"A Kinetic Comparison\non the Inhibition of Adenosine Deaminase by Purine Drugs","volume":"6","author":"Ataiea","year":"2007","journal-title":"Iran. J. Pharm. Res."}],"container-title":["Journal of Chemical Information and Modeling"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/ci5004224","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jcisd8\/article-pdf\/54\/9\/2570\/10079463\/ci5004224.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jcisd8\/article-pdf\/54\/9\/2570\/10079463\/ci5004224.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,28]],"date-time":"2026-09-28T09:09:15Z","timestamp":1790586555000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jcisd8\/article\/54\/9\/2570\/941369\/Topology-of-the-Interactions-Pattern-in"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2014,9,3]]},"references-count":88,"journal-issue":{"issue":"9","published-online":{"date-parts":[[2014,9,3]]},"published-print":{"date-parts":[[2014,9,22]]}},"URL":"https:\/\/doi.org\/10.1021\/ci5004224","relation":{},"ISSN":["1549-9596","1549-960X"],"issn-type":[{"value":"1549-9596","type":"print"},{"value":"1549-960X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2014,9,3]]}}}