{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,6]],"date-time":"2025-11-06T00:38:44Z","timestamp":1762389524290,"version":"3.40.5"},"reference-count":80,"publisher":"American Chemical Society (ACS)","issue":"11","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Org. Chem."],"published-print":{"date-parts":[[2012,6,1]]},"DOI":"10.1021\/jo3003776","type":"journal-article","created":{"date-parts":[[2012,5,21]],"date-time":"2012-05-21T16:59:24Z","timestamp":1337619564000},"page":"4968-4979","source":"Crossref","is-referenced-by-count":22,"title":["A Non-Karplus Effect: Evidence from Phosphorus Heterocycles and DFT Calculations of the Dependence of Vicinal Phosphorus\u2013Hydrogen NMR Coupling Constants on Lone-Pair Conformation"],"prefix":"10.1021","volume":"77","author":[{"given":"William H.","family":"Hersh","sequence":"first","affiliation":[{"name":"Department of Chemistry and Biochemistry, Queens College and the Graduate Center of the City University of New York, Flushing, New York 11367-1597,\rUnited States"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sherrell T.","family":"Lam","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry, Queens College and the Graduate Center of the City University of New York, Flushing, New York 11367-1597,\rUnited States"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Daniel J.","family":"Moskovic","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry, Queens College and the Graduate Center of the City University of New York, Flushing, New York 11367-1597,\rUnited States"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Antonios J.","family":"Panagiotakis","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry, Queens College and the Graduate Center of the City University of New York, Flushing, New York 11367-1597,\rUnited States"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"316","published-online":{"date-parts":[[2012,5,23]]},"reference":[{"key":"ref1\/cit1","doi-asserted-by":"crossref","first-page":"11","DOI":"10.1063\/1.1729860","volume":"30","author":"Karplus M.","year":"1959","journal-title":"J. Chem. Phys."},{"key":"ref2\/cit2","doi-asserted-by":"crossref","first-page":"2870","DOI":"10.1021\/ja00901a059","volume":"85","author":"Karplus M.","year":"1963","journal-title":"J. Am. Chem. Soc."},{"key":"ref3\/cit3","first-page":"1825","author":"Benezra C.","year":"1966","journal-title":"Bull. Soc. Chim. Fr."},{"key":"ref4\/cit4","doi-asserted-by":"crossref","first-page":"6890","DOI":"10.1021\/ja00802a003","volume":"95","author":"Benezra C.","year":"1973","journal-title":"J. Am. Chem. Soc."},{"key":"ref5\/cit5","doi-asserted-by":"crossref","first-page":"1830","DOI":"10.1021\/j100726a032","volume":"73","author":"Bothner-By A. A.","year":"1969","journal-title":"J. Phys. Chem."},{"key":"ref6\/cit6","doi-asserted-by":"crossref","first-page":"4071","DOI":"10.1016\/S0040-4020(01)82939-2","volume":"25","author":"Kainosho M.","year":"1969","journal-title":"Tetrahedron"},{"key":"ref7\/cit7","first-page":"111","volume":"3","author":"White D. W.","year":"1970","journal-title":"J. Magn. Reson."},{"key":"ref8\/cit8","doi-asserted-by":"crossref","first-page":"2257","DOI":"10.3891\/acta.chem.scand.25-2257","volume":"25","author":"Bergesen K.","year":"1971","journal-title":"Acta Chem. Scand."},{"key":"ref9\/cit9","doi-asserted-by":"crossref","first-page":"2873","DOI":"10.1021\/ja00790a023","volume":"95","author":"Blackburn B. J.","year":"1973","journal-title":"J. Am. Chem. Soc."},{"key":"ref10\/cit10","doi-asserted-by":"crossref","first-page":"3541","DOI":"10.1021\/ja00428a026","volume":"98","author":"Lee C.-H.","year":"1976","journal-title":"J. Am. Chem. Soc."},{"key":"ref11\/cit11","doi-asserted-by":"crossref","first-page":"1387","DOI":"10.1080\/07391102.1984.10507527","volume":"1","author":"Lankhorst P. P.","year":"1984","journal-title":"J. Biomol. Struct. Dyn."},{"key":"ref12\/cit12","doi-asserted-by":"crossref","first-page":"1315","DOI":"10.1021\/cr00029a007","volume":"94","author":"Gorenstein D. G.","year":"1994","journal-title":"Chem. Rev."},{"key":"ref13\/cit13","doi-asserted-by":"crossref","first-page":"35","DOI":"10.1046\/j.1432-1327.1999.00639.x","volume":"265","author":"Ojha R. P.","year":"1999","journal-title":"Eur. J. Biochem."},{"key":"ref14\/cit14","doi-asserted-by":"crossref","first-page":"1455","DOI":"10.1246\/bcsj.74.1455","volume":"74","author":"Oikawa M.","year":"2001","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref15\/cit15","doi-asserted-by":"crossref","first-page":"59","DOI":"10.1080\/10406630500519395","volume":"26","author":"Sakamoto Y.","year":"2006","journal-title":"Polycyclic Aromat. Compd."},{"key":"ref16\/cit16","doi-asserted-by":"crossref","first-page":"425","DOI":"10.1016\/S0022-5193(74)80010-X","volume":"48","author":"Giessner-Prettre C.","year":"1974","journal-title":"J. Theor. Biol."},{"key":"ref17\/cit17","doi-asserted-by":"crossref","first-page":"751","DOI":"10.1016\/0022-5193(78)90282-5","volume":"72","author":"Giessner-Prettre C.","year":"1978","journal-title":"J. Theor. Biol."},{"key":"ref18\/cit18","doi-asserted-by":"crossref","first-page":"3136","DOI":"10.1021\/ja00529a042","volume":"102","author":"Quin L. D.","year":"1980","journal-title":"J. Am. Chem. Soc."},{"key":"ref19\/cit19","doi-asserted-by":"crossref","first-page":"6235","DOI":"10.1021\/jo00075a018","volume":"58","author":"Huang Y.","year":"1993","journal-title":"J. Org. Chem."},{"key":"ref20\/cit20","first-page":"3719","author":"Gagnaire D.","year":"1966","journal-title":"Bull. Soc. Chim. Fr."},{"key":"ref21\/cit21","first-page":"2240","author":"Gagnaire D.","year":"1967","journal-title":"Bull. Soc. Chim. Fr."},{"key":"ref22\/cit22","first-page":"2392","author":"Gagnaire D.","year":"1968","journal-title":"Bull. Soc. Chim. Fr."},{"key":"ref23\/cit23","doi-asserted-by":"crossref","first-page":"1085","DOI":"10.1021\/ja00707a070","volume":"92","author":"Cowley A. H.","year":"1970","journal-title":"J. Am. Chem. Soc."},{"key":"ref24\/cit24","doi-asserted-by":"crossref","first-page":"4593","DOI":"10.1016\/S0040-4039(00)89426-5","volume":"11","author":"Albrand J.-P.","year":"1970","journal-title":"Tetrahedron Lett."},{"key":"ref25\/cit25","doi-asserted-by":"crossref","first-page":"4902","DOI":"10.1021\/ja00769a018","volume":"94","author":"Robert J. B.","year":"1972","journal-title":"J. Am. Chem. Soc."},{"key":"ref26\/cit26","doi-asserted-by":"crossref","first-page":"3261","DOI":"10.1016\/S0040-4039(01)94018-3","volume":"13","author":"Bushweller C. H.","year":"1972","journal-title":"Tetrahedron Lett."},{"key":"ref27\/cit27","doi-asserted-by":"crossref","first-page":"8222","DOI":"10.1021\/ja00778a045","volume":"94","author":"Bentrude W. G.","year":"1972","journal-title":"J. Am. Chem. Soc."},{"key":"ref28\/cit28","doi-asserted-by":"crossref","first-page":"4666","DOI":"10.1021\/ja00795a033","volume":"95","author":"Bentrude W. G.","year":"1973","journal-title":"J. Am. Chem. Soc."},{"key":"ref29\/cit29","doi-asserted-by":"crossref","first-page":"573","DOI":"10.1021\/ja00836a018","volume":"97","author":"Bentrude W. G.","year":"1975","journal-title":"J. Am. Chem. Soc."},{"key":"ref30\/cit30","first-page":"365","volume-title":"Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis","author":"Bentrude W. G.","year":"1987"},{"key":"ref31\/cit31","first-page":"41","volume-title":"Phosphorus-31 NMR Spectral Properties in Compound Characterization and Structural Analysis","author":"Bentrude W. G.","year":"1994"},{"key":"ref32\/cit32","doi-asserted-by":"crossref","first-page":"4767","DOI":"10.1021\/jo00120a020","volume":"60","author":"Huang Y.","year":"1995","journal-title":"J. Org. Chem."},{"key":"ref33\/cit33","doi-asserted-by":"crossref","first-page":"409","DOI":"10.1002\/mrc.1260270502","volume":"27","author":"Gil V. M. S.","year":"1989","journal-title":"Magn. Reson. Chem."},{"key":"ref34\/cit34","doi-asserted-by":"crossref","first-page":"384","DOI":"10.1021\/ic9713801","volume":"37","author":"Hersh W. H.","year":"1998","journal-title":"Inorg. Chem."},{"key":"ref35\/cit35","doi-asserted-by":"crossref","first-page":"7355","DOI":"10.1021\/jo049057k","volume":"69","author":"Hersh W. H.","year":"2004","journal-title":"J. Org. Chem."},{"key":"ref36\/cit36","doi-asserted-by":"crossref","first-page":"2153","DOI":"10.1021\/jo035508+","volume":"69","author":"Hersh W. H.","year":"2004","journal-title":"J. Org. Chem."},{"key":"ref37\/cit37","doi-asserted-by":"crossref","first-page":"635","DOI":"10.1016\/0040-4020(77)80303-7","volume":"33","author":"Garrigues B.","year":"1977","journal-title":"Tetrahedron"},{"key":"ref38\/cit38","doi-asserted-by":"crossref","first-page":"47","DOI":"10.1080\/03086647808079964","volume":"4","author":"Munoz A.","year":"1978","journal-title":"Phosphorus Sulfur"},{"key":"ref39\/cit39","first-page":"241","volume":"75","author":"Lamande L.","year":"1993","journal-title":"Phosphorus, Sulfur Silicon"},{"key":"ref40\/cit40","doi-asserted-by":"crossref","first-page":"2021","DOI":"10.1039\/a702813j","author":"Fu H.","year":"1997","journal-title":"J. Chem. Soc., Perkin Trans. 1"},{"key":"ref41\/cit41","doi-asserted-by":"crossref","first-page":"376","DOI":"10.1055\/s-1998-2050","author":"Zhang N. J.","year":"1998","journal-title":"Synthesis"},{"key":"ref42\/cit42","doi-asserted-by":"crossref","first-page":"855","DOI":"10.1055\/s-1998-2086","author":"Fu H.","year":"1998","journal-title":"Synthesis"},{"key":"ref43\/cit43","doi-asserted-by":"crossref","first-page":"65","DOI":"10.1016\/S0022-2860(02)00002-9","volume":"610","author":"Lu K.","year":"2002","journal-title":"J. Mol. Struct."},{"key":"ref44\/cit44","unstructured":"Eliel, E. L.; Wilen, S. H.; Mander, L. N.InStereochemistry of Organic Compounds;Wiley-Interscience:New York, 1994; pp541\u2013542."},{"key":"ref45\/cit45","doi-asserted-by":"crossref","first-page":"1709","DOI":"10.1021\/jo00268a038","volume":"54","author":"Setzer W. N.","year":"1989","journal-title":"J. Org. Chem."},{"key":"ref46\/cit46","doi-asserted-by":"crossref","first-page":"2081","DOI":"10.1039\/P29910002081","author":"Schwalbe C. H.","year":"1991","journal-title":"J. Chem. Soc., Perkin Trans. 2"},{"key":"ref47\/cit47","doi-asserted-by":"crossref","first-page":"9151","DOI":"10.1021\/ja00781a028","volume":"94","author":"Hutchins R. O.","year":"1972","journal-title":"J. Am. Chem. Soc."},{"volume-title":"Gaussian 03, Revision D.01 and Gaussian 09, Revision A.02","year":"2009","author":"Frisch M. J.","key":"ref48\/cit48"},{"key":"ref49\/cit49","unstructured":"Foresman, J. B.; Frisch, \u00c6.Exploring Chemistry with Electronic Structure Methods,2nded.Gaussian, Inc.:Pittsburgh, 1996; p52."},{"key":"ref50\/cit50","unstructured":"Cheeseman, J. R.; Frisch, \u00c6.Technical Support Information: Predicting Magnetic Properties with ChemDraw and Gaussian.http:\/\/www.gaussian.com\/g_whitepap\/nmrcomp.htm."},{"key":"ref51\/cit51","doi-asserted-by":"crossref","first-page":"15370","DOI":"10.1021\/jp0480955","volume":"108","author":"Salvador P.","year":"2004","journal-title":"J. Phys. Chem. B"},{"key":"ref52\/cit52","doi-asserted-by":"crossref","first-page":"4921","DOI":"10.1002\/ejoc.200400447","author":"T\u00e4htinen P.","year":"2004","journal-title":"Eur. J. Org. Chem."},{"key":"ref53\/cit53","doi-asserted-by":"crossref","first-page":"1028","DOI":"10.1021\/ct600110u","volume":"2","author":"Deng W.","year":"2006","journal-title":"J. Chem. Theory Comput."},{"key":"ref54\/cit54","unstructured":"Subramaniam, G.; Hersh, W. H., unpublished work."},{"key":"ref55\/cit55","doi-asserted-by":"crossref","first-page":"1360","DOI":"10.1021\/ct600166u","volume":"2","author":"Jensen F.","year":"2006","journal-title":"J. Chem. Theory Comput."},{"key":"ref56\/cit56","doi-asserted-by":"crossref","first-page":"115","DOI":"10.1016\/0166-1280(89)85138-3","volume":"184","author":"Elguero J.","year":"1989","journal-title":"J. Mol. Struct. (THEOCHEM)"},{"key":"ref57\/cit57","doi-asserted-by":"crossref","first-page":"7861","DOI":"10.1021\/ja00178a003","volume":"112","author":"Bindal R. D.","year":"1990","journal-title":"J. Am. Chem. Soc."},{"key":"ref58\/cit58","doi-asserted-by":"crossref","first-page":"9803","DOI":"10.1021\/j100177a038","volume":"95","author":"Nicholas J. B.","year":"1991","journal-title":"J. Phys. Chem."},{"key":"ref59\/cit59","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1007\/BF02263522","volume":"6","author":"Nyul\u00e1szi L.","year":"1995","journal-title":"Struct. Chem."},{"key":"ref60\/cit60","doi-asserted-by":"crossref","first-page":"347","DOI":"10.1002\/9780470871737.ch6","volume-title":"The Chemistry of Anilines, Part 1","author":"Kolehmainen E.","year":"2007"},{"key":"ref61\/cit61","doi-asserted-by":"crossref","first-page":"210","DOI":"10.1006\/jmsp.1994.1186","volume":"166","author":"Dr\u00e9an P.","year":"1994","journal-title":"J. Mol. Spectrosc."},{"key":"ref62\/cit62","doi-asserted-by":"crossref","first-page":"1805","DOI":"10.1021\/ja00752a035","volume":"93","author":"Egan W.","year":"1971","journal-title":"J. Am. Chem. Soc."},{"key":"ref63\/cit63","doi-asserted-by":"crossref","first-page":"151","DOI":"10.1080\/10426500108040240","volume":"174","author":"Yavari I.","year":"2001","journal-title":"Phosphorus, Sulfur Silicon Relat. Elem."},{"key":"ref64\/cit64","first-page":"1869","volume":"46","author":"Jug\u00e9 S.","year":"1990","journal-title":"Acta Crystallogr."},{"key":"ref65\/cit65","doi-asserted-by":"crossref","first-page":"3090","DOI":"10.1021\/ja00713a028","volume":"92","author":"Baechler R. D.","year":"1970","journal-title":"J. Am. Chem. Soc."},{"key":"ref66\/cit66","doi-asserted-by":"crossref","first-page":"62","DOI":"10.1016\/j.ica.2010.11.022","volume":"369","author":"Mukhlall J. A.","year":"2011","journal-title":"Inorg. Chim. Acta"},{"key":"ref67\/cit67","doi-asserted-by":"crossref","first-page":"15668","DOI":"10.1021\/ja0306718","volume":"126","author":"Thibaudeau C.","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ref68\/cit68","doi-asserted-by":"crossref","first-page":"9781","DOI":"10.1021\/ja040251y","volume":"127","author":"Klepach T. E.","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"ref69\/cit69","doi-asserted-by":"crossref","first-page":"7071","DOI":"10.1021\/jo0619884","volume":"72","author":"Zhao H.","year":"2007","journal-title":"J. Org. Chem."},{"key":"ref70\/cit70","doi-asserted-by":"crossref","first-page":"2243","DOI":"10.1039\/b705761j","volume":"5","author":"Mobli M.","year":"2007","journal-title":"Org. Biomol. Chem."},{"key":"ref71\/cit71","doi-asserted-by":"crossref","first-page":"4899","DOI":"10.1021\/jo100521g","volume":"75","author":"Hu X.","year":"2010","journal-title":"J. Org. Chem."},{"key":"ref72\/cit72","doi-asserted-by":"crossref","first-page":"3744","DOI":"10.1021\/cr030733c","volume":"107","author":"Bifulco G.","year":"2007","journal-title":"Chem. Rev."},{"key":"ref73\/cit73","doi-asserted-by":"crossref","first-page":"4017","DOI":"10.1021\/jo900482q","volume":"74","author":"Jain R.","year":"2009","journal-title":"J. Org. Chem."},{"key":"ref74\/cit74","doi-asserted-by":"crossref","first-page":"1411","DOI":"10.1002\/ejoc.200901255","volume":"2010","author":"Di Micco S.","year":"2010","journal-title":"Eur. J. Org. Chem."},{"key":"ref75\/cit75","doi-asserted-by":"crossref","first-page":"6072","DOI":"10.1021\/ja201108a","volume":"133","author":"Saielli G.","year":"2011","journal-title":"J. Am. Chem. Soc."},{"key":"ref76\/cit76","doi-asserted-by":"crossref","first-page":"4818","DOI":"10.1021\/jo200513q","volume":"76","author":"Bally T.","year":"2011","journal-title":"J. Org. Chem."},{"key":"ref77\/cit77","doi-asserted-by":"crossref","first-page":"6057","DOI":"10.1021\/jo200637g","volume":"76","author":"L\u00f3pez-Vallejo F.","year":"2011","journal-title":"J. Org. Chem."},{"key":"ref78\/cit78","doi-asserted-by":"crossref","first-page":"1116","DOI":"10.1021\/ja01285a046","volume":"59","author":"McChesney E. W.","year":"1937","journal-title":"J. Am. Chem. Soc."},{"key":"ref79\/cit79","unstructured":"Clemente, F. R.Personal Communication, Technical Support, Gaussian, Inc. 2008."},{"key":"ref80\/cit80","doi-asserted-by":"crossref","first-page":"199","DOI":"10.1080\/17415993.2011.580346","volume":"32","author":"Mukhlall J. A.","year":"2011","journal-title":"J. Sulfur Chem."}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jo3003776","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,4,13]],"date-time":"2023-04-13T20:54:12Z","timestamp":1681419252000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/jo3003776"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2012,5,23]]},"references-count":80,"journal-issue":{"issue":"11","published-print":{"date-parts":[[2012,6,1]]}},"alternative-id":["10.1021\/jo3003776"],"URL":"https:\/\/doi.org\/10.1021\/jo3003776","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"type":"print","value":"0022-3263"},{"type":"electronic","value":"1520-6904"}],"subject":[],"published":{"date-parts":[[2012,5,23]]}}}