{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,23]],"date-time":"2026-03-23T15:28:08Z","timestamp":1774279688914,"version":"3.50.1"},"reference-count":99,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2015,1,20]],"date-time":"2015-01-20T00:00:00Z","timestamp":1421712000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>3-Aminomethylation of salicylalkylamides afforded hybrids with a Mannich base. In addition, it triggered the rotation of the amide bond. The observed conformational switch is driven by strong intramolecular hydrogen bonding between the Mannich base and phenolic group. Crystal structure analysis reveals the stabilization of the hybrid molecules by double hydrogen bonding of the phenolic OH, which acts as an acceptor and donor simultaneously. The molecules contain an amide site and a Mannich base site in an orthogonal spatial arrangement. The intramolecular hydrogen bonds are persistent in a nonpolar solvent (e.g., chloroform). The conformational change can be reversed upon protection or protonation of the Mannich base nitrogen.<\/jats:p>","DOI":"10.3390\/molecules20011686","type":"journal-article","created":{"date-parts":[[2015,1,20]],"date-time":"2015-01-20T12:36:22Z","timestamp":1421757382000},"page":"1686-1711","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Hybrids of Salicylalkylamides and Mannich Bases: Control of the Amide Conformation by Hydrogen Bonding in Solution and in the Solid State"],"prefix":"10.3390","volume":"20","author":[{"given":"Christian","family":"Dank","sequence":"first","affiliation":[{"name":"Institute of Medical Chemistry, Center of Pathobiochemistry and Genetics,  Medical University of Vienna, W\u00e4hringerstrasse 10, Vienna 1090, Austria"},{"name":"Institute of Organic Chemistry, University of Vienna, W\u00e4hringerstrasse 38, Vienna 1090, Austria"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Barbara","family":"Kirchknopf","sequence":"additional","affiliation":[{"name":"University of Applied Sciences Wiener Neustadt, Konrad-Lorenz-Strasse 10,  Tulln a. d. Donau 3430, Austria"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Matthias","family":"Mastalir","sequence":"additional","affiliation":[{"name":"Institute of Medical Chemistry, Center of Pathobiochemistry and Genetics,  Medical University of Vienna, W\u00e4hringerstrasse 10, Vienna 1090, Austria"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hanspeter","family":"K\u00e4hlig","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry, University of Vienna, W\u00e4hringerstrasse 38, Vienna 1090, Austria"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Susanne","family":"Felsinger","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry, University of Vienna, W\u00e4hringerstrasse 38, Vienna 1090, Austria"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alexander","family":"Roller","sequence":"additional","affiliation":[{"name":"Structure Analysis Centre, University of Vienna, W\u00e4hringerstrasse 38, Vienna 1090, Austria"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Vladimir","family":"Arion","sequence":"additional","affiliation":[{"name":"Structure Analysis Centre, University of Vienna, W\u00e4hringerstrasse 38, Vienna 1090, Austria"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hubert","family":"Gstach","sequence":"additional","affiliation":[{"name":"Institute of Medical Chemistry, Center of Pathobiochemistry and Genetics,  Medical University of Vienna, W\u00e4hringerstrasse 10, Vienna 1090, Austria"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2015,1,20]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"211","DOI":"10.2174\/157019311795177808","article-title":"Salicylanilides and Their Derivates as Perspective Anti-tuberculosis Drugs: Synthetic Routes and Biological Evaluations","volume":"8","author":"Pauk","year":"2011","journal-title":"Mini Rev. Org. Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"6106","DOI":"10.1016\/j.ejmech.2010.09.040","article-title":"New amino acid esters of salicylanilides active against MDR-TB and other microbes","volume":"45","author":"Buchta","year":"2010","journal-title":"Eur. J. Med. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"2939","DOI":"10.1021\/jm9803572","article-title":"Substituted salicylanilides as inhibitors of two-component regulatory systems in bacteria","volume":"41","author":"Macielag","year":"1998","journal-title":"J. Med. Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"1923","DOI":"10.1016\/S0960-894X(98)00326-6","article-title":"Novel inhibitors of bacterial two component systems with gram positive antibacterial activity: Pharmacophore identification based on the screening hit closantel","volume":"8","author":"Hlasta","year":"1998","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1693","DOI":"10.1128\/AAC.43.7.1693","article-title":"Multiple mechanism of action for inhibitors of histidine protein kinases from bacterial two-component systems","volume":"43","author":"Hillard","year":"1999","journal-title":"Antimicrob. Agents Chemother."},{"key":"ref_6","first-page":"121","article-title":"Synthesis and antimycobacterial activity of salicylanilides substituted in position 5","volume":"55","author":"Waisser","year":"2001","journal-title":"Chem. Pap."},{"key":"ref_7","first-page":"5007","article-title":"Salicylanilide esterification: Unexpected formation of novel seven-membered rings","volume":"29","author":"Pour","year":"2006","journal-title":"Tetrahedron Lett."},{"key":"ref_8","first-page":"1","article-title":"Salicylanilide Acetates: Synthesis and Antibacterial Evaluation","volume":"12","author":"Buchta","year":"2007","journal-title":"Molecules"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"3572","DOI":"10.1016\/j.bmc.2009.04.008","article-title":"New Antituberculotics Originated from Salicylanilides with Promising In vitro Activity against Atypical Mycobacterial Strains","volume":"17","author":"Kunc","year":"2009","journal-title":"Bioorg. Med. Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"348","DOI":"10.1016\/j.bmcl.2008.11.080","article-title":"Salicylanilide esters of N-protected amino acids as novel antimicrobial agents","volume":"19","author":"Buchta","year":"2009","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"1054","DOI":"10.1016\/j.bmc.2009.12.055","article-title":"Salicylanilide carbamates: Antitubercular agents active against multidrug-resistant Mycobacterium tuberculosis strains","volume":"18","author":"Kunc","year":"2010","journal-title":"Bioorg. Med. Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1023","DOI":"10.1248\/yakushi1947.102.11_1023","article-title":"On the antimicrobial activity and syntheses of carbanilide and salicylanilide derivatives","volume":"102","author":"Takeuchi","year":"1982","journal-title":"Yakugaku Zasshi"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"956","DOI":"10.2174\/138955711797068382","article-title":"Antiviral Activity of Substituted Salicylanilides\u2014A Review","volume":"11","year":"2011","journal-title":"Mini Rev. Med. Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"3173","DOI":"10.1016\/j.bmcl.2008.04.068","article-title":"Identification of halosalicylamide derivatives as a novel class of allosteric inhibitors of HCV NS5B polymerase","volume":"18","author":"Liu","year":"2008","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"e1002976","DOI":"10.1371\/journal.ppat.1002976","article-title":"Niclosamide Is a Proton Carrier and Targets Acidic Endosomes with Broad Antiviral Effects","volume":"8","author":"Jurgeit","year":"2012","journal-title":"PLoS Pathog."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1649","DOI":"10.1016\/S0960-894X(00)00335-8","article-title":"Salicylamide inhibitors of influenza virus fusion","volume":"10","author":"Combrink","year":"2000","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"2177","DOI":"10.1016\/S0960-894X(99)00361-3","article-title":"Novel quinolizidine salicylamide influenza fusion inhibitors","volume":"9","author":"Yu","year":"1999","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_18","first-page":"826","article-title":"Synthesis of 5-chloro-3'-nitro-4-substituted salicylanilides, a new series of anthelmintic and antimicrobial agents","volume":"20","author":"Singh","year":"1977","journal-title":"J. Org. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"3295","DOI":"10.1021\/jm00115a020","article-title":"Synthesis and biological activity of a series of diaryl susbtituted alpha-cyano-beta hydroxypenamides, a new class of anthelmintic agents","volume":"34","author":"Sjogren","year":"1991","journal-title":"J. Med. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"305","DOI":"10.1038\/nature09107","article-title":"Thousands of chemical starting points for antimalarial lead identification","volume":"465","author":"Gamo","year":"2010","journal-title":"Nature"},{"key":"ref_21","unstructured":"Gstach, H., Chiba, P., and Mastalir, M. (2013). WO 2013186153 A2."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"3168","DOI":"10.1016\/j.bmcl.2011.02.100","article-title":"Synthesis of benzologues of Nitazoxanide and Tizoxanide: A comparative study of their in vitro broad-spectrum antiprotozoal activity","volume":"21","year":"2011","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"3088","DOI":"10.1021\/jm2015183","article-title":"Synthesis, Biological Evaluation, and Structure-Activity Relationships of N-Benzoyl-2-hydroxybenzamides as Agents Active against P. falciparum (K1 strain), Trypanosomes, and Leishmania","volume":"55","author":"Stec","year":"2012","journal-title":"J. Med. Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"322","DOI":"10.1002\/ardp.200300725","article-title":"Anti mycobacterial and antifungal isosters of salicylamides","volume":"336","author":"Waisser","year":"2003","journal-title":"Arch. Pharm. Med. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"201","DOI":"10.1002\/ardp.19943270402","article-title":"Salicylanilides containg amino-acid or pyran moieties with molluscicidal activity","volume":"327","author":"Nawwar","year":"1994","journal-title":"Arch. Pharm. (Weinheim)"},{"key":"ref_26","first-page":"245","article-title":"Synthesis and molluscicidal activity of some anilides","volume":"22","author":"Shoeb","year":"1980","journal-title":"Egypt. J. Chem."},{"key":"ref_27","first-page":"787","article-title":"Crystallographic, theoretical and molecular modelling studies on the conformations of the salicylamide, raclopride, a selective dopamine-D2 antagonist","volume":"39","author":"Norinder","year":"1987","journal-title":"J. Pharm. Pharmacol."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"937","DOI":"10.1016\/S0969-2126(94)00095-6","article-title":"Crystal structure of scytalone dehydratase\u2014A disease determinant of the rice pathogen, magnaporthe grisea","volume":"2","author":"Lundqvist","year":"1994","journal-title":"Structure"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"8760","DOI":"10.1016\/j.bmc.2008.07.024","article-title":"Salicylanilides: Selective inhibitors of interleukin-12p40 production","volume":"16","author":"Brown","year":"2008","journal-title":"Bioorg. Med. Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"1775","DOI":"10.1021\/bc800078q","article-title":"Identification of 14\u20133-3z by Chemical Affinity with Salicylanilide Inhibitors of Interleukin-12p40 Production","volume":"19","author":"Boyce","year":"2008","journal-title":"Bioconjugate Chem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"469","DOI":"10.1016\/j.bmcl.2005.06.088","article-title":"Acryloylamino-salicylanilides as EGFR PTK inhibitors","volume":"16","author":"Deng","year":"2006","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"5403","DOI":"10.1021\/jm200325s","article-title":"Discovery and Structure Activity Relationships of Modified Salicylanilides as Cell Permeable Inhibitors of Poly(ADP-ribose) Glycohydrolase (PARG)","volume":"54","author":"Steffen","year":"2011","journal-title":"J. Med. Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"1670","DOI":"10.1021\/jm020292+","article-title":"Synthesis, anticancer activity, and inhibition of tubulin polymerization by conformationally restricted analogues of lavendustin A","volume":"46","author":"Mu","year":"2003","journal-title":"J. Med. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"1275","DOI":"10.1135\/cccc20031275","article-title":"On the relationship between the structure and antimycobacterial activity of substituted N-benzylsalicylamides","volume":"68","author":"Waisser","year":"2003","journal-title":"Collect. Czechoslov. Chem. Commun."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"9947","DOI":"10.1021\/jo701823d","article-title":"Anion-Triggered Substituent-Dependent Conformational Switching of Salicylanilides. New Hints for Understanding the Inhibitory Mechanism of Salicylanilides","volume":"72","author":"Guo","year":"2007","journal-title":"J. Org. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"2335","DOI":"10.1246\/bcsj.73.2335","article-title":"Studies on the conformations of antimicrobial salicylanilide derivatives by spectroscopy","volume":"73","author":"Suezawa","year":"2000","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"849","DOI":"10.1107\/S0108768100003694","article-title":"Intramolecular hydrogen bonds: Common motifs, probabilities of formation and implications for supramolecular organization","volume":"56","author":"Bilton","year":"2000","journal-title":"Acta Crystallogr. Sect. B"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"2601","DOI":"10.1021\/jm100087s","article-title":"Intramolecular hydrogen bonding in medicinal chemistry","volume":"53","author":"Kuhn","year":"2010","journal-title":"J. Med. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"1605","DOI":"10.1016\/S0960-894X(00)80026-8","article-title":"A diazine heterocycle replaces a six-membered hydrogen-bonded array in the active site of scytalone dehydratase","volume":"3","author":"Hodge","year":"1993","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"11","DOI":"10.1016\/j.ejmech.2003.09.010","article-title":"Salicylanilides as inhibitors of the protein tyrosine kinase epidermal growth factor receptor","volume":"39","author":"Liechti","year":"2004","journal-title":"Eur. J. Med. Chem."},{"key":"ref_41","first-page":"167","article-title":"The aminoquinazoline group as a replacement for the salicylamide group: The design and synthesis of a novel highly selective \u03b21 adrenoceptor partial agonist","volume":"9","author":"Block","year":"1992","journal-title":"Drug Des. Discov."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"2967","DOI":"10.1016\/S0960-894X(03)00626-7","article-title":"Identification of a new chemical class of potent angiogenesis inhibitors based on conformational considerations and database searching","volume":"13","author":"Furet","year":"2003","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"4418","DOI":"10.1021\/ol901785v","article-title":"Novel Amphiphilic \u03b1-Helix Mimetics","volume":"11","author":"Marimganti","year":"2009","journal-title":"Org. Lett."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"10590","DOI":"10.1021\/ja050886c","article-title":"Abiotic metallofoldamers as electrochemically responsive molecules","volume":"127","author":"Zhang","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"283","DOI":"10.1021\/jp410370q","article-title":"Chiroptical Inversion Induced by Rotation of a Carbon\u2013Carbon Single Bond: An Experimental and Theoretical Study","volume":"118","author":"Lu","year":"2014","journal-title":"J. Phys. Chem. A"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"264","DOI":"10.1016\/j.molstruc.2007.04.038","article-title":"Structural changes caused by the conversion of 2-hydroxybenzamide (salicylamide) into the oxyanion","volume":"875","author":"Velcheva","year":"2008","journal-title":"J. Mol. Struct."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"2057","DOI":"10.1246\/bcsj.77.2057","article-title":"Structures of the small-molecule bcl-2 inhibitor (BH3I-2) and its related simple model in protonated and deprotonated forms","volume":"77","author":"Kanamori","year":"2004","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"969","DOI":"10.1002\/anie.200461842","article-title":"Linear-to-Turn Conformational Switching Induced by Deprotonation of Unsymmetrically Linked Phenolic Oligoamides","volume":"44","author":"Kanamori","year":"2005","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"9","DOI":"10.1016\/S0022-2860(96)09323-4","article-title":"Conformational properties of o-alkoxy-benzamides in different solvents","volume":"384","author":"Cignitti","year":"1996","journal-title":"J. Mol. Struct."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1016\/j.molstruc.2006.03.029","article-title":"Structural and energetic consequences of the formation of intramolecular hydrogen bonds","volume":"790","author":"Koll","year":"2006","journal-title":"J. Mol. Struct."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"81","DOI":"10.1016\/j.molstruc.2004.07.008","article-title":"Theoretical study on the intramolecular hydrogen bond in chloro-substituted N,N-dimethylaminomethylphenols. I. Structural effects","volume":"700","author":"Koll","year":"2004","journal-title":"J. Mol. Struct."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"127","DOI":"10.1016\/S0022-2860(00)00682-7","article-title":"Spectroscopic and structural consequences of intramolecular hydrogen bond formation in ortho-dimethylaminomethylphenol","volume":"559","author":"Koll","year":"2001","journal-title":"J. Mol. Struct."},{"key":"ref_53","first-page":"983","article-title":"Mannich bases as model compounds for intramolecular hydrogen bonding. Part 2. Structure and properties in solution","volume":"130","author":"Koll","year":"1999","journal-title":"Monatsh. Chem."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"475","DOI":"10.1007\/BF00807072","article-title":"Mannich bases as model compounds for intramolecular hydrogen bonding I. Solid state structures and molecular calculations","volume":"127","author":"Koll","year":"1996","journal-title":"Monatsh. Chem."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"1003","DOI":"10.1007\/BF00808772","article-title":"1H-NMR investigations of the conformation of aryl-(hydroxynaphthyl)-methylpiperidines. Intramolecular interactions, IV","volume":"120","author":"Ansari","year":"1989","journal-title":"Monatsh. Chem."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"563","DOI":"10.1007\/BF00903309","article-title":"Intramolecular interactions I. The use of some Mannich bases of naphthols as model compounds for intramolecular hydrogen bonding","volume":"111","author":"Haslinger","year":"1980","journal-title":"Monatsh. Chem."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"1045","DOI":"10.1002\/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO;2-E","article-title":"Modern variants of the mannich reaction","volume":"37","author":"Arend","year":"1998","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"19","DOI":"10.1016\/0378-5173(86)90195-X","article-title":"Prodrugs as drug delivery systems. o-Acyloxymethyl salicylamide N-Mannich bases as double prodrug forms for amines","volume":"29","author":"Bundgaard","year":"1986","journal-title":"Int. J. Pharm."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"119","DOI":"10.1016\/0378-5173(80)90056-3","article-title":"Pro-drugs as drug delivery systems xiii. Kinetics of decomposition of n-mannich bases of salicylamide and assessment of their suitability as possible pro-drugs for amines","volume":"7","author":"Johansen","year":"1980","journal-title":"Int. J. Pharm."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"992","DOI":"10.1002\/ardp.19673001204","article-title":"Configuration of the mannich bases of amides and methyl esters of \u03b2-resorcylic, gentisic, and 2-hydroxy-2-naphthoic acids","volume":"300","author":"Brandes","year":"1967","journal-title":"Arch. Pharm. (Weinheim)"},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"241","DOI":"10.1007\/s00706-004-0226-2","article-title":"Chemistry of phosphorus ylides. Part 22. Effect of newly synthesized niclosamide mannich bases, phosphopyranones, phosphoranylidenes, and oxaphosphinin on some metabolic aspects of biomphalaria alexandrina","volume":"136","author":"Soliman","year":"2005","journal-title":"Monatsh. Chem."},{"key":"ref_62","first-page":"164","article-title":"Acid amides in the mannich reaction. II. Aminomethylation of salicyl- and 5-chlorosalicylamides","volume":"1","author":"Stavrovskaya","year":"1967","journal-title":"Chem. Abstr."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"521","DOI":"10.1246\/bcsj.52.521","article-title":"Spectroscopic studies of solvent effects on intramolecular hydrogen bonding in N-substituted salicylamides","volume":"52","author":"Kondo","year":"1979","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"2790","DOI":"10.1246\/bcsj.45.2790","article-title":"The nuclear magnetic resonance study of several o-Disubstituted Benzenes","volume":"45","author":"Kondo","year":"1972","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"809","DOI":"10.1007\/BF00808374","article-title":"O-H...O(S) hydrogen bonds in 2-hydroxy(thio)benzamides. Survey of spectroscopic and structural data","volume":"121","author":"Steinwender","year":"1990","journal-title":"Monatsh. Chem."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"6358","DOI":"10.1021\/jo901065y","article-title":"The scope and limitation of nickel-catalyzed aminocarbonylation of aryl bromides from formamide derivatives","volume":"74","author":"Jo","year":"2009","journal-title":"J. Org. Chem."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"12809","DOI":"10.1021\/jp905261p","article-title":"Intramolecular Hydrogen Bonding in ortho-Substituted Arylamide Oligomers: A Computational and Experimental Study of ortho-Fluoro- and ortho-Chloro-N-methylbenzamides","volume":"113","author":"Galan","year":"2009","journal-title":"J. Phys. Chem. B"},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"11883","DOI":"10.1039\/c3cp50353d","article-title":"Conformational preferences of furan- and thiophene-based arylamides: A combined computational and experimental study","volume":"15","author":"Galan","year":"2013","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"5607","DOI":"10.1021\/ja990904o","article-title":"A New Approach for the Design of Supramolecular Recognition Units: Hydrogen-Bonded Molecular Duplexes","volume":"121","author":"Gong","year":"1999","journal-title":"J. Am. Chem. Soc."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"7041","DOI":"10.1021\/jp902155j","article-title":"Hydrogen Bonding in ortho-Substituted Arylamides: The Influence of Protic Solvents","volume":"113","author":"Liu","year":"2009","journal-title":"J. Phys. Chem."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"226","DOI":"10.1063\/1.1743676","article-title":"Theory of nuclear magnetic shielding in molecules. I. Long-range dipolar shielding of protons","volume":"27","author":"McConnell","year":"1957","journal-title":"J. Chem. Phys."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"899","DOI":"10.1002\/anie.196608992","article-title":"Magnetic Anisotropy of the Amide Group","volume":"5","author":"Paulsen","year":"1966","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"2577","DOI":"10.1139\/v68-420","article-title":"Proton magnetic resonance spectra of some aromatic amines and derived amides","volume":"46","author":"Brown","year":"1968","journal-title":"Can. J. Chem."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"706","DOI":"10.1002\/hlca.19840670310","article-title":"NMR Conformational Study of Aminoalkylbenzamides, Aminoalkyl-o-Anisamides, and Metoclopramide, a Dopamine Receptor Antagonist","volume":"67","author":"Anker","year":"1984","journal-title":"Helv. Chim. Acta"},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"119","DOI":"10.1016\/0040-4020(70)85014-1","article-title":"NMR\u2014The chemical shift\u2014IV: The anisotropies of the carbonyl group","volume":"26","author":"ApSimon","year":"1970","journal-title":"Tetrahedron"},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"517","DOI":"10.1021\/cr60267a001","article-title":"Nuclear magnetic resonance studies of amides","volume":"70","author":"Stewart","year":"1970","journal-title":"Chem. Rev."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"844","DOI":"10.1002\/mrc.1414","article-title":"13C and 1H nuclear magnetic resonance of methyl-substituted acetophenones and methyl benzoates: Steric hindrance and inhibited conjugation","volume":"42","author":"Cigler","year":"2004","journal-title":"Magn. Res. Chem."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"308","DOI":"10.1039\/C3RA45512B","article-title":"New insight into the anisotropic effects in solution-state NMR spectroscopy","volume":"4","year":"2014","journal-title":"RSC Adv."},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"3513","DOI":"10.1021\/cr030083c","article-title":"Interrelation between H-bond and Pi-Electron Delocalization","volume":"105","author":"Sobczyk","year":"2005","journal-title":"Chem. Rev."},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"65","DOI":"10.1016\/j.molstruc.2005.10.046","article-title":"The intramolecular hydrogen bond in 2-hydroxy-benzamides","volume":"790","author":"Kawski","year":"2006","journal-title":"J. Mol. Struct."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"1077","DOI":"10.1055\/s-1993-26001","article-title":"Superelectrophilic Tscherniac Amidomethylation of Aromatics with N-Hydroxymethylphthalimide in Trifluoromethanesulfonic Acid","volume":"11","author":"Olah","year":"1993","journal-title":"Synthesis"},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"14","DOI":"10.1021\/jo00838a005","article-title":"Tscherniac-Einhorn reaction. II. Kinetics and mechanism","volume":"34","author":"Zaugg","year":"1969","journal-title":"J. Org. Chem."},{"key":"ref_83","first-page":"1011","article-title":"Synthesis and biological evaluation of 3-(phthalimidomethyl)- 4-(5-substituted isoxazoline and pyrazoline) substituted benzanilides","volume":"84","author":"Sahu","year":"2007","journal-title":"J. Indian Chem. Soc."},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"940","DOI":"10.1246\/bcsj.37.940","article-title":"Crystal structure of salicylamide","volume":"37","author":"Sasada","year":"1964","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"129","DOI":"10.1007\/BF00809525","article-title":"Crystal Structures and Hydrogen Bonding Schemes in Four Benzamide Derivatives (2-Hydroxy-benzamide, 2-Hydroxy-thiobenzamide, 2-Hydroxy-N,N-dimethyl-benzamide, and 2-Hydroxy-N,N-dimethyl-thiobenzamide","volume":"121","author":"Pertlik","year":"1990","journal-title":"Monatsh. Chem."},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"17","DOI":"10.1524\/zkri.1992.202.1-2.17","article-title":"Crystal structure of 2-hydroxy-N-methylbenzamide and 2-hydroxy-N-methylthiobenzamide","volume":"202","author":"Pertlik","year":"1992","journal-title":"Z. Kristallogr."},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"349","DOI":"10.3390\/cryst2020349","article-title":"Crystal Structure of the 5-Chloro Salicylamides: Three Different Types of the H-bonding Influenced Linear Chain Formation in the Solid State","volume":"2","author":"Imramovsky","year":"2012","journal-title":"Crystalls"},{"key":"ref_88","doi-asserted-by":"crossref","first-page":"o884","DOI":"10.1107\/S1600536808010453","article-title":"N-Benzyl-2-hydroxybenzamide","volume":"64","author":"Zhang","year":"2008","journal-title":"Acta Crystallogr. Sect. E"},{"key":"ref_89","first-page":"491","article-title":"Intra- versus intermolecular hydrogen bonds in salicylamide derivatives","volume":"18","author":"Etter","year":"1988","journal-title":"J. Chem. Cryst."},{"key":"ref_90","doi-asserted-by":"crossref","first-page":"3034","DOI":"10.1021\/jp311003d","article-title":"Hydrogen Bonding in the Gas-Phase: The Molecular Structures of 2-Hydroxybenzamide (C7H7NO2) and 2-Methoxybenzamide (C8H9NO2), Obtained by Gas-Phase Electron Diffraction and Theoretical Calculations","volume":"117","author":"Aarset","year":"2013","journal-title":"J. Phys. Chem."},{"key":"ref_91","doi-asserted-by":"crossref","first-page":"o1911","DOI":"10.1107\/S1600536808028286","article-title":"Tetrakis[2-(benzylaminocarbonyl)phenoxymethyl]-methane","volume":"64","author":"Song","year":"2008","journal-title":"Acta Crystallogr. Sect. E"},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"48","DOI":"10.1002\/1521-3773(20020104)41:1<48::AID-ANIE48>3.0.CO;2-U","article-title":"The hydrogen bond in the solid state","volume":"41","author":"Steiner","year":"2002","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_93","doi-asserted-by":"crossref","unstructured":"Geffrey, G.A., and Saenger, W. (1991). Hydrogen Bonding in Biological Structures, Springer.","DOI":"10.1007\/978-3-642-85135-3"},{"key":"ref_94","doi-asserted-by":"crossref","first-page":"7512","DOI":"10.1021\/jo971176v","article-title":"NMR chemical shifts of common laboratory solvents as trace impurities","volume":"62","author":"Gottlieb","year":"1997","journal-title":"J. Org. Chem."},{"key":"ref_95","doi-asserted-by":"crossref","first-page":"560","DOI":"10.1002\/jps.2600580507","article-title":"Comparative stability of benzamide, salicylamide, and some N-substituted derivatives","volume":"58","author":"Koshy","year":"1969","journal-title":"J. Pharm. Sci."},{"key":"ref_96","doi-asserted-by":"crossref","first-page":"o4276","DOI":"10.1107\/S1600536806034994","article-title":"2-(hydroxy\u00admethyl)isoindoline-1,3-dione","volume":"62","author":"Li","year":"2006","journal-title":"Acta Crystallogr. Sect. E"},{"key":"ref_97","unstructured":"Pressprich, M.R., and Chambers, J. (2004). SAINT-Plus, Bruker-Nonius AXS Inc.. version 7.06a and APEX2."},{"key":"ref_98","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1107\/S0108767307043930","article-title":"A short history of shelx","volume":"64","author":"Sheldrick","year":"2008","journal-title":"Acta Crystallogr. Sect. A"},{"key":"ref_99","doi-asserted-by":"crossref","first-page":"565","DOI":"10.1107\/S0021889897003117","article-title":"ORTEP-3 for windows\u2014A version of ORTEP-III with a graphical user interface (GUI)","volume":"30","author":"Farrugia","year":"1997","journal-title":"J. Appl. Crystallogr."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/20\/1\/1686\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T20:41:49Z","timestamp":1760215309000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/20\/1\/1686"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2015,1,20]]},"references-count":99,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2015,1]]}},"alternative-id":["molecules20011686"],"URL":"https:\/\/doi.org\/10.3390\/molecules20011686","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2015,1,20]]}}}