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Here, 15N\/13C spin-echo magic-angle spinning (MAS) solid-state nuclear magnetic resonance (NMR) experiments are applied to \u201cview\u201d intermolecular CH\u00b7\u00b7\u00b7N hydrogen bonding in two selectively labeled organic compounds, 4-[15N] cyano-4\u2032-[13C2] ethynylbiphenyl (1) and [15N3,13C6]-2,4,6-triethynyl-1,3,5-triazine (2). The synthesis of 2-15N3,13C6 is reported here for the first time via a multistep procedure, where the key element is the reaction of [15N3]-2,4,6-trichloro-1,3,5-triazine (5) with [13C2]-[(trimethylsilyl)ethynyl]zinc chloride (8) to afford its immediate precursor [15N3,13C6]-2,4,6-tris[(trimethylsilyl)ethynyl]-1,3,5-triazine (9). Experimentally determined hydrogen-bond-mediated 2hJCN couplings (4.7 \u00b1 0.4 Hz (1) and 4.1 \u00b1 0.3 Hz (2)) are compared with density functional theory (DFT) gauge-including projector augmented wave (GIPAW) calculations, whereby species-independent coupling values 2hKCN (29.0 \u00d7 1019 kg m\u20132 s\u20132 A\u20132 (1) and 27.9 \u00d7 1019 kg m\u20132 s\u20132 A\u20132 (2)) quantitatively demonstrate the J couplings for these \u201cweak\u201d CH\u00b7\u00b7\u00b7N hydrogen bonds to be of a similar magnitude to those for conventionally observed NH\u00b7\u00b7\u00b7O hydrogen-bonding interactions in uracil (2hKNO: 28.1 and 36.8 \u00d7 1019 kg m\u20132 s\u20132 A\u20132). Moreover, the GIPAW calculations show a clear correlation between increasing 2hJCN (and 3hJCN) coupling and reducing C(H)\u00b7\u00b7\u00b7N and H\u00b7\u00b7\u00b7N hydrogen-bonding distances, with the Fermi contact term accounting for at least 98% of the isotropic 2hJCN coupling.<\/jats:p>","DOI":"10.1021\/acs.jpca.9b10726","type":"journal-article","created":{"date-parts":[[2019,12,27]],"date-time":"2019-12-27T10:05:26Z","timestamp":1577441126000},"page":"560-572","source":"Crossref","is-referenced-by-count":36,"title":["Weak Intermolecular CH\u00b7\u00b7\u00b7N Hydrogen Bonding: Determination of 13CH\u201315N Hydrogen-Bond Mediated\n                    <i>J<\/i>\n                    Couplings by\nSolid-State NMR Spectroscopy and First-Principles Calculations"],"prefix":"10.1021","volume":"124","author":[{"given":"Amy L.","family":"Webber","sequence":"first","affiliation":[{"name":"University of Warwick , , ,","place":["Coventry, U.K., CV4 7AL"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jonathan R.","family":"Yates","sequence":"additional","affiliation":[{"name":"University of Oxford , , Parks Road , ,","place":["Oxford, U.K., OX1 3PH"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Miri","family":"Zilka","sequence":"additional","affiliation":[{"name":"University of Warwick , , ,","place":["Coventry, U.K., CV4 7AL"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Simone","family":"Sturniolo","sequence":"additional","affiliation":[{"name":"Rutherford Appleton Laboratory , , Chilton, , ,","place":["Didcot, Oxfordshire, U.K., OX11 0QX"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anne-Christine","family":"Uldry","sequence":"additional","affiliation":[{"name":"University of Bern , , Freiburgstrasse 15 , ,","place":["Bern, Switzerland, 3010"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Emily K.","family":"Corlett","sequence":"additional","affiliation":[{"name":"University of Warwick , , ,","place":["Coventry, U.K., CV4 7AL"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chris J.","family":"Pickard","sequence":"additional","affiliation":[{"name":"University of Cambridge , , 27 Charles Babbage Road , ,","place":["Cambridge, U.K., CB3 0FS"]},{"name":"Tohoku University , 2-1-1 Katahira , Aoba, ,","place":["Sendai, Japan, 980-8577"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marta","family":"Pe\u0301rez-Torralba","sequence":"additional","affiliation":[{"name":"Facultad de Ciencias, UNED , , Senda del Rey 9 , ,","place":["Madrid, Spain, E-28040"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"M.","family":"Angeles Garcia","sequence":"additional","affiliation":[{"name":"Facultad de Ciencias, UNED , , Senda del Rey 9 , ,","place":["Madrid, Spain, E-28040"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dolores","family":"Santa Maria","sequence":"additional","affiliation":[{"name":"Facultad de Ciencias, UNED , , Senda del Rey 9 , ,","place":["Madrid, Spain, E-28040"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6634-2677","authenticated-orcid":true,"given":"Rosa M.","family":"Claramunt","sequence":"additional","affiliation":[{"name":"Facultad de Ciencias, UNED , , Senda del Rey 9 , ,","place":["Madrid, Spain, E-28040"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2069-8496","authenticated-orcid":true,"given":"Steven P.","family":"Brown","sequence":"additional","affiliation":[{"name":"University of Warwick , , ,","place":["Coventry, U.K., CV4 7AL"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2019,12,27]]},"reference":[{"key":"2026090219363406400_cit1","doi-asserted-by":"publisher","first-page":"52","DOI":"10.1002\/anie.201002960","article-title":"A bond\nby any other name","volume":"50","author":"Desiraju","year":"2011","journal-title":"Angew. 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Chem.\nPhys."},{"key":"2026090219363406400_cit59","doi-asserted-by":"publisher","DOI":"10.1063\/1.2801984","article-title":"A first principles\ntheory of nuclear magnetic resonance J-coupling in solid-state systems","volume":"127","author":"Joyce","year":"2007","journal-title":"J. Chem. Phys."},{"key":"2026090219363406400_cit60","doi-asserted-by":"publisher","first-page":"3865","DOI":"10.1103\/PhysRevLett.77.3865","article-title":"Generalized\ngradient approximation made simple","volume":"77","author":"Perdew","year":"1996","journal-title":"Phys. Rev.\nLett."},{"key":"2026090219363406400_cit61","doi-asserted-by":"publisher","first-page":"654","DOI":"10.1107\/S0567740877004415","article-title":"Neutron-diffraction\nstudy of l-histidine hydrochloride monohydrate","volume":"33","author":"Fuess","year":"1977","journal-title":"Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem."},{"key":"2026090219363406400_cit62","doi-asserted-by":"publisher","first-page":"64","DOI":"10.1016\/j.ssnmr.2016.05.004","article-title":"Visualization and processing of computed\nsolid-state NMR parameters: MagresView and MagresPython","volume":"78","author":"Sturniolo","year":"2016","journal-title":"Solid State Nucl. Magn. Reson."},{"key":"2026090219363406400_cit63","doi-asserted-by":"publisher","first-page":"539","DOI":"10.1002\/jlcr.579","article-title":"A facile preparation of (2,4,6-C-14-cyanuric\nacid under solvent-free conditions","volume":"45","author":"Patil","year":"2002","journal-title":"J. Labelled\nCompd. Radiopharm."},{"key":"2026090219363406400_cit64","doi-asserted-by":"crossref","first-page":"357","DOI":"10.1002\/jlac.18601160308","article-title":"Notiz u\u0308ber die Einwirkung\ndes Phosphorsuperchlorides auf Cyanursa\u0308ure","volume":"116","author":"Beilstein","year":"1860","journal-title":"Justus Liebigs Ann. Chem."},{"key":"2026090219363406400_cit65","doi-asserted-by":"publisher","first-page":"358","DOI":"10.1021\/jo00396a046","article-title":"General synthesis of\nterminal and internal arylalkynes by palladium-catalyzed reaction\nof alkynylzinc reagents with aryl halides","volume":"43","author":"King","year":"1978","journal-title":"J.\nOrg. Chem."},{"key":"2026090219363406400_cit66","doi-asserted-by":"publisher","first-page":"2419","DOI":"10.1021\/ol016274o","article-title":"Synthesis of differentially substituted hexaethynylbenzenes based\non tandem Sonogashira and Negishi cross-coupling reactions","volume":"3","author":"Sonoda","year":"2001","journal-title":"Org. Lett."},{"key":"2026090219363406400_cit67","doi-asserted-by":"publisher","first-page":"636","DOI":"10.1021\/cm00041a014","article-title":"Synthesis of ethynyl-substituted\nprecursors to carbon-nitrogen sulfur extended structures - reactions\nof C3N3F3 and C2N2SCl2 with alkali-metal (trimethylsilyl)acetylides","volume":"6","author":"Kouvetakis","year":"1994","journal-title":"Chem. Mater."},{"key":"2026090219363406400_cit68","doi-asserted-by":"publisher","first-page":"183","DOI":"10.1006\/jmra.1993.1089","article-title":"NMR lineshapes\narising from a pair of nonequivalent homonuclear spins in magic-angle-spinning\nexperiments","volume":"102","author":"Wu","year":"1993","journal-title":"J. Magn. Reson., Ser. A"},{"key":"2026090219363406400_cit69","doi-asserted-by":"publisher","first-page":"90","DOI":"10.1016\/S1090-7807(02)00174-X","article-title":"Carbon-13 lineshapes in solid-state NMR of labeled\ncompounds. Effects of coherent CSA-dipolar cross-correlation","volume":"162","author":"Duma","year":"2003","journal-title":"J. Magn. Reson."},{"key":"2026090219363406400_cit70","doi-asserted-by":"publisher","first-page":"637","DOI":"10.1016\/0022-2364(89)90359-4","article-title":"The observation of two-dimensional\nNMR-spectra of crystalline solids - the 31P CP-MAS COSY\nand J-resolved spectra of a phosphine complex of Hg(II)","volume":"83","author":"Allman","year":"1989","journal-title":"J. Magn. Reson."},{"key":"2026090219363406400_cit71","doi-asserted-by":"publisher","first-page":"7156","DOI":"10.1063\/1.458255","article-title":"One-dimensional\nand 2-dimensional 31P cross-polarization magic-angle-spinning\nnuclear-magnetic-resonance studies on 2-spin systems with homonuclear\ndipolar coupling and j coupling","volume":"92","author":"Kubo","year":"1990","journal-title":"J. Chem. Phys."},{"key":"2026090219363406400_cit72","doi-asserted-by":"publisher","first-page":"145","DOI":"10.1021\/ic00027a030","article-title":"Homonuclear 31P J-resolved 2d spectra of\nrhodium(i) phosphine complexes in the solid-state","volume":"31","author":"Wu","year":"1992","journal-title":"Inorg. Chem."},{"key":"2026090219363406400_cit73","doi-asserted-by":"publisher","first-page":"4535","DOI":"10.1002\/1521-3773(20021202)41:23&lt;4535::AID-ANIE4535&gt;3.0.CO;2-O","article-title":"Observation of a H-agostic bond in\na highly active rhenium- alkylidene olefin metathesis heterogeneous\ncatalyst by two- dimensional solid-state NMR spectroscopy","volume":"41","author":"Lesage","year":"2002","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090219363406400_cit74","doi-asserted-by":"publisher","first-page":"2234","DOI":"10.1021\/cm031009d","article-title":"Characterization of\nthe room-temperature structure of SnP2O7 by 31P through-space and through-bond NMR correlation spectroscopy","volume":"15","author":"Fayon","year":"2003","journal-title":"Chem. Mater."},{"key":"2026090219363406400_cit75","doi-asserted-by":"publisher","first-page":"1089","DOI":"10.1016\/j.solidstatesciences.2004.04.019","article-title":"Frequency-selective measurement of\nheteronuclear scalar couplings in solid-state NMR","volume":"6","author":"Tre\u0301bosc","year":"2004","journal-title":"Solid State Sci."},{"key":"2026090219363406400_cit76","doi-asserted-by":"publisher","first-page":"43","DOI":"10.1016\/j.jmr.2004.07.022","article-title":"The 2D MAS NMR spin-echo experiment: the determination\nof 13C-13C J couplings in a solid-state cellulose\nsample","volume":"171","author":"Brown","year":"2004","journal-title":"J. Magn. Reson."},{"key":"2026090219363406400_cit77","doi-asserted-by":"publisher","first-page":"11861","DOI":"10.1021\/ja902238s","article-title":"31P MAS\nrefocused INADEQUATE spin-echo (REINE) NMR spectroscopy: Revealing\nj coupling and chemical shift two-dimensional correlations in disordered\nsolids","volume":"131","author":"Guerry","year":"2009","journal-title":"J. Am. Chem. Soc."},{"key":"2026090219363406400_cit78","doi-asserted-by":"publisher","first-page":"90","DOI":"10.1016\/j.jmr.2013.03.010","article-title":"Selective measurements\nof long-range homonuclear J-couplings in solid-state\nNMR","volume":"231","author":"Thureau","year":"2013","journal-title":"J. Magn. Reson."},{"key":"2026090219363406400_cit79","doi-asserted-by":"publisher","first-page":"196","DOI":"10.1016\/0022-2364(89)90280-1","article-title":"Rotational-echo double-resonance\nNMR","volume":"81","author":"Gullion","year":"1989","journal-title":"J. Magn. Reson."},{"key":"2026090219363406400_cit80","doi-asserted-by":"publisher","DOI":"10.1063\/1.4773016","article-title":"Benchmarking density-functional theory calculations of NMR shielding\nconstants and spin-rotation constants using accurate coupled-cluster\ncalculations","volume":"138","author":"Teale","year":"2013","journal-title":"J. Chem. Phys."},{"key":"2026090219363406400_cit81","doi-asserted-by":"publisher","first-page":"107","DOI":"10.1080\/00268976.2013.802820","article-title":"Ramsey terms for two-, three-, and\nfour-bond coupling involving 15N and 17O in\nhydrogen-bonded and nonhydrogen-bonded systems: are coupling constants\nsensitive to RAHBs?","volume":"112","author":"Elguero","year":"2014","journal-title":"Mol. Phys."},{"key":"2026090219363406400_cit82","doi-asserted-by":"publisher","DOI":"10.1063\/1.4913639","article-title":"Relativistic\nfour-component calculations of indirect nuclear spin-spin couplings\nwith efficient evaluation of the exchange-correlation response kernel","volume":"142","author":"Kr\u030ci\u0301stkova\u0301","year":"2015","journal-title":"J. Chem. Phys."},{"key":"2026090219363406400_cit83","doi-asserted-by":"publisher","first-page":"24119","DOI":"10.1039\/C6CP04853F","article-title":"NMR spin-spin coupling constants: bond angle dependence\nof the sign and magnitude of the vicinal 3JHF coupling","volume":"18","author":"Viesser","year":"2016","journal-title":"Phys. Chem. Chem. Phys."},{"key":"2026090219363406400_cit84","doi-asserted-by":"publisher","first-page":"12663","DOI":"10.1021\/ja800419m","article-title":"Density functional\ntheory calculations of hydrogen-bond-mediated NMR J coupling in the\nsolid state","volume":"130","author":"Joyce","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"2026090219363406400_cit85","doi-asserted-by":"publisher","first-page":"3971","DOI":"10.1039\/C7SC00587C","article-title":"Determination of a complex crystal structure in the\nabsence of single crystals: analysis of powder X-ray diffraction data,\nguided by solid-state NMR and periodic DFT calculations, reveals a\nnew 2\u2032-deoxyguanosine structural motif","volume":"8","author":"Hughes","year":"2017","journal-title":"Chem. Sci."},{"key":"2026090219363406400_cit86","doi-asserted-by":"publisher","first-page":"S86","DOI":"10.1002\/mrc.2635","article-title":"New perspectives in the PAW\/GIPAW approach: J(P-O-Si) coupling constants,\nantisymmetric parts of shift tensors and NQR predictions","volume":"48","author":"Bonhomme","year":"2010","journal-title":"Magn. Reson. Chem."},{"key":"2026090219363406400_cit87","doi-asserted-by":"publisher","first-page":"5778","DOI":"10.1039\/c0cp02343d","article-title":"Towards homonuclear J solid-state NMR correlation experiments\nfor half-integer quadrupolar nuclei: experimental and simulated 11B MAS spin-echo dephasing and calculated 2JBB coupling constants for lithium diborate","volume":"13","author":"Barrow","year":"2011","journal-title":"Phys. Chem. Chem. Phys."},{"key":"2026090219363406400_cit88","doi-asserted-by":"publisher","first-page":"6172","DOI":"10.1021\/jacs.5b03353","article-title":"Unusual intermolecular \u201cthrough-space\u201d\nJ couplings in P-Se heterocycles","volume":"137","author":"Sanz Camacho","year":"2015","journal-title":"J. Am. Chem.\nSoc."},{"key":"2026090219363406400_cit89","doi-asserted-by":"publisher","first-page":"10881","DOI":"10.1021\/acs.inorgchem.6b01121","article-title":"Investigating unusual\nhomonuclear intermolecular \u201cthrough-space\u201d J couplings in organochalcogen systems","volume":"55","author":"Sanz Camacho","year":"2016","journal-title":"Inorg.\nChem."},{"key":"2026090219363406400_cit90","doi-asserted-by":"publisher","first-page":"6019","DOI":"10.1021\/ja9908321","article-title":"Internucleotide scalar\ncouplings across hydrogen bonds in Watson-Crickand Hoogsteen base\npairs of a DNA triplex","volume":"121","author":"Dingley","year":"1999","journal-title":"J. Am. Chem. Soc."},{"key":"2026090219363406400_cit91","doi-asserted-by":"publisher","first-page":"8661","DOI":"10.1021\/ja9917417","article-title":"Quantum-chemical characterization of nuclear spin-spin\ncouplings across hydrogen bonds","volume":"121","author":"Scheurer","year":"1999","journal-title":"J. Am. Chem.\nSoc."},{"key":"2026090219363406400_cit92","doi-asserted-by":"publisher","first-page":"8105","DOI":"10.1021\/jp001251x","article-title":"The shielding constants and scalar couplings in N\u2013H...O\u2550C\nand N\u2013H...N\u2550C hydrogen bonded systems: An ab initio\nMO study","volume":"104","author":"Pecul","year":"2000","journal-title":"J. Phys. Chem. A"},{"key":"2026090219363406400_cit93","doi-asserted-by":"publisher","first-page":"4014","DOI":"10.1021\/ja003781c","article-title":"A DFT study of the\ninterresidue dependencies of scalar J-coupling and magnetic shielding\nin the hydrogen-bonding regions of a DNA tripler","volume":"123","author":"Barfield","year":"2001","journal-title":"J. Am. Chem. Soc."},{"key":"2026090219363406400_cit94","doi-asserted-by":"publisher","first-page":"3560","DOI":"10.1021\/ja994312h","article-title":"Predicted\nNMR coupling constants across hydrogen bonds: A fingerprint for specifying\nhydrogen bond type?","volume":"122","author":"Del Bene","year":"2000","journal-title":"J. Am. Chem. Soc."},{"key":"2026090219363406400_cit95","doi-asserted-by":"publisher","first-page":"7930","DOI":"10.1063\/1.481394","article-title":"Comprehensive ab initio studies of\nnuclear magnetic resonance shielding and coupling constants in XH...O\nhydrogen-bonded complexes of simple organic molecules","volume":"112","author":"Pecul","year":"2000","journal-title":"J. Chem. Phys."},{"key":"2026090219363406400_cit96","doi-asserted-by":"publisher","first-page":"421","DOI":"10.1002\/mrc.1386","article-title":"Predicted\nsigns of reduced two-bond spin-spin coupling constants (2hKX-Y) across X-H-Y hydrogen bonds","volume":"42","author":"Del Bene","year":"2004","journal-title":"Magn. Reson. Chem."},{"key":"2026090219363406400_cit97","doi-asserted-by":"publisher","first-page":"4335","DOI":"10.1002\/anie.200351713","article-title":"Visualization of\nnuclear spin-spin coupling pathways by real-space functions","volume":"42","author":"Malkina","year":"2003","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090219363406400_cit98","doi-asserted-by":"publisher","first-page":"4838","DOI":"10.1021\/cr400330g","article-title":"Indirect\nnonbonded nuclear spin\u2013spin coupling: A guide for the recognition\nand understanding of \u201cthrough-space\u201d NMR J constants in small organic, organometallic, and coordination compounds","volume":"114","author":"Hierso","year":"2014","journal-title":"Chem. Rev."},{"key":"2026090219363406400_cit99","doi-asserted-by":"publisher","first-page":"2532","DOI":"10.1002\/1521-3773(20010702)40:13&lt;2532::AID-ANIE2532&gt;3.0.CO;2-E","article-title":"DFT calculation\nof intermolecular nuclear spin-spin coupling in van der Waals dimers","volume":"40","author":"Bagno","year":"2001","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090219363406400_cit100","doi-asserted-by":"publisher","first-page":"2047","DOI":"10.1002\/1521-3765(20020503)8:9&lt;2047::AID-CHEM2047&gt;3.0.CO;2-Z","article-title":"Through-space\nspin-spin coupling in van der waals dimers and CH\/pi interacting systems.\nAn ab initio and DFT study","volume":"8","author":"Bagno","year":"2002","journal-title":"Chem. - Eur. J."},{"key":"2026090219363406400_cit101","doi-asserted-by":"publisher","first-page":"3194","DOI":"10.1021\/jacs.7b13345","article-title":"Direct observation of CH\/CH van der\nWaals interactions in proteins by NMR","volume":"140","author":"Li","year":"2018","journal-title":"J. Am.\nChem. Soc."},{"key":"2026090219363406400_cit102","doi-asserted-by":"publisher","first-page":"1715","DOI":"10.1021\/ja00895a002","article-title":"A survey of\nC\u2013H groups as proton donors in hydrogen bonding","volume":"85","author":"Allerhand","year":"1963","journal-title":"J. Am. Chem. 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