{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T18:56:12Z","timestamp":1760295372295},"reference-count":32,"publisher":"Wiley","issue":"5","license":[{"start":{"date-parts":[[2004,9,7]],"date-time":"2004-09-07T00:00:00Z","timestamp":1094515200000},"content-version":"vor","delay-in-days":3417,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J Comput Chem"],"published-print":{"date-parts":[[1995,5]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The conformational preferences of oxymethylpyridines have been investigated by <jats:italic>ab initio<\/jats:italic> calculations and compared to similar calculations for oxymethylbenzene. The C\uf8ffO bond in the pyridine compounds was found to prefer eclipsing with a C\uf8ffC bond in the ring, in agreement with previous observations but in disaccord with tentative MM2 calculations. The effect was most pronounced in the 2\u2010substituted pyridine. The benzene compound, on the other hand, showed good agreement between the energies from MM2, MM3, and <jats:italic>ab initio<\/jats:italic> calculations. The conformational preferences are discussed in terms of stereoelectronic interactions. New MM2 and MM3 parameters were determined from <jats:italic>ab initio<\/jats:italic> calculations on nonstationary points on the energy hypersurface. The parameterization method is discussed. \u00a9 1995 by John Wiley &amp; Sons, Inc.<\/jats:p>","DOI":"10.1002\/jcc.540160510","type":"journal-article","created":{"date-parts":[[2005,1,2]],"date-time":"2005-01-02T01:09:09Z","timestamp":1104628149000},"page":"620-627","source":"Crossref","is-referenced-by-count":16,"title":["Unusual conformational\u2010determining interactions in oxymethylpyridines: An <i>ab initio<\/i> study and an improved method for refining molecular mechanics parameters"],"prefix":"10.1002","volume":"16","author":[{"given":"Per\u2010Ola","family":"Norrby","sequence":"first","affiliation":[]},{"given":"Kenneth","family":"W\u00e4rnmark","sequence":"additional","affiliation":[]},{"given":"Bj\u00f6rn","family":"\u00c5kermark","sequence":"additional","affiliation":[]},{"given":"Christina","family":"Moberg","sequence":"additional","affiliation":[]}],"member":"311","published-online":{"date-parts":[[2004,9,7]]},"reference":[{"key":"e_1_2_1_2_2","series-title":"ACS Monograph 177","volume-title":"Molecular Mechanics","author":"Burkert U.","year":"1982"},{"key":"e_1_2_1_3_2","unstructured":"N. L.Allinger lecture notes ACS short course June1993."},{"key":"e_1_2_1_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic00275a005"},{"key":"e_1_2_1_4_3","doi-asserted-by":"publisher","DOI":"10.1021\/jo00010a030"},{"key":"e_1_2_1_4_4","first-page":"2171","volume":"47","author":"Cs\u00f6regh I.","year":"1991","journal-title":"Acta Cryst."},{"key":"e_1_2_1_4_5","doi-asserted-by":"publisher","DOI":"10.1016\/S0020-1693(00)82899-6"},{"key":"e_1_2_1_4_6","doi-asserted-by":"publisher","DOI":"10.1021\/jo00087a012"},{"key":"e_1_2_1_4_7","unstructured":"(f)A.Ertan I.Cs\u00f6regh H.Adolfsson andC.Moberg accepted for publication inActa Cryst. C;"},{"key":"e_1_2_1_4_8","doi-asserted-by":"publisher","DOI":"10.1021\/jo00190a022"},{"key":"e_1_2_1_5_2","unstructured":"MM2(91) version for Macintosh: MacMimic\/MM2(91) In\u2010Star Software AB IDEON Research Park S\u2010223 70 Lund Sweden. MM2 versions for platforms other than Macintosh are available from the Quantum Chemistry Program Exchange University of Indiana Bloomington IN 47405. Parameters for the only unknown structural element (dihedral angle type 6\u20101\u20102\u201037) were initially set to zero by analogy with similar existing values (for dihedral angle type 6\u20101\u20102\u20102)."},{"key":"e_1_2_1_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00064a054"},{"key":"e_1_2_1_6_3","unstructured":"(b)M.Sj\u00f6gren Selective Control in Transition Metal\u2010Catalyzed Nucleophilic Substitution of Allylic Leaving Groups Ph.D. thesis The Royal Institute of Technology September1993;"},{"key":"e_1_2_1_6_4","doi-asserted-by":"publisher","DOI":"10.1021\/ja00098a006"},{"key":"e_1_2_1_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00036a003"},{"key":"e_1_2_1_7_3","doi-asserted-by":"publisher","DOI":"10.1021\/jo00067a002"},{"key":"e_1_2_1_7_4","first-page":"227","volume-title":"Catalytic Asymmetric Synthesis","author":"Johnson R. A.","year":"1993"},{"key":"e_1_2_1_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00271a002"},{"key":"e_1_2_1_8_3","doi-asserted-by":"publisher","DOI":"10.1021\/ja00203a001"},{"key":"e_1_2_1_8_4","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199006391"},{"key":"e_1_2_1_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19921250528"},{"key":"e_1_2_1_9_3","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)96219-1"},{"key":"e_1_2_1_9_4","doi-asserted-by":"publisher","DOI":"10.1016\/0022-328X(90)87185-G"},{"key":"e_1_2_1_9_5","doi-asserted-by":"publisher","DOI":"10.1016\/S0957-4166(00)82080-7"},{"key":"e_1_2_1_9_6","first-page":"339","volume":"122","author":"Falorni M.","year":"1992","journal-title":"Gazz. Chim. Ital."},{"key":"e_1_2_1_10_2","doi-asserted-by":"crossref","first-page":"2065","DOI":"10.3987\/COM-89-5146","volume":"11","author":"Soai K.","year":"1989","journal-title":"Heterocycles"},{"key":"e_1_2_1_10_3","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(91)80656-Q"},{"key":"e_1_2_1_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/om00115a022"},{"key":"e_1_2_1_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.540150207"},{"key":"e_1_2_1_13_2","volume-title":"Gaussian 92, Revision B","author":"Frisch M. J.","year":"1992"},{"key":"e_1_2_1_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.540060517"},{"key":"e_1_2_1_15_2","volume-title":"Stereoelectronic Effects in Organic Chemistry","author":"Deslongchamps P.","year":"1983"},{"key":"e_1_2_1_16_2","unstructured":"Spartan 3.0 from Wavefunction Inc. 18401 Von Karman #370 Irvine CA 92715."}],"container-title":["Journal of Computational Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fjcc.540160510","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/jcc.540160510","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,25]],"date-time":"2023-10-25T20:02:51Z","timestamp":1698264171000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/jcc.540160510"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[1995,5]]},"references-count":32,"journal-issue":{"issue":"5","published-print":{"date-parts":[[1995,5]]}},"alternative-id":["10.1002\/jcc.540160510"],"URL":"https:\/\/doi.org\/10.1002\/jcc.540160510","archive":["Portico"],"relation":{},"ISSN":["0192-8651","1096-987X"],"issn-type":[{"value":"0192-8651","type":"print"},{"value":"1096-987X","type":"electronic"}],"subject":[],"published":{"date-parts":[[1995,5]]}}}