Portal de Periódicos da CAPES

Molecular mechanics (MM4) calculations on alkenes

1996; Wiley; Volume: 17; Issue: 5-6 Linguagem: Inglês

10.1002/(sici)1096-987x(199604)17

1096-987X

Neysa Nevins, Kuohsiang Chen, Norman L. Allinger,

Molecular Spectroscopy and Structure

Journal of Computational ChemistryVolume 17, Issue 5-6 p. 669-694 Molecular mechanics (MM4) calculations on alkenes† Neysa Nevins, Neysa Nevins Computational Center for Molecular Structure and Design, Department of Chemistry, University of Georgia, Athens, Georgia 30602-2556Search for more papers by this authorKuohsiang Chen, Kuohsiang Chen Computational Center for Molecular Structure and Design, Department of Chemistry, University of Georgia, Athens, Georgia 30602-2556Search for more papers by this authorNorman L. Allinger, Corresponding Author Norman L. Allinger Computational Center for Molecular Structure and Design, Department of Chemistry, University of Georgia, Athens, Georgia 30602-2556Computational Center for Molecular Structure and Design, Department of Chemistry, University of Georgia, Athens, Georgia 30602-2556Search for more papers by this author Neysa Nevins, Neysa Nevins Computational Center for Molecular Structure and Design, Department of Chemistry, University of Georgia, Athens, Georgia 30602-2556Search for more papers by this authorKuohsiang Chen, Kuohsiang Chen Computational Center for Molecular Structure and Design, Department of Chemistry, University of Georgia, Athens, Georgia 30602-2556Search for more papers by this authorNorman L. Allinger, Corresponding Author Norman L. Allinger Computational Center for Molecular Structure and Design, Department of Chemistry, University of Georgia, Athens, Georgia 30602-2556Computational Center for Molecular Structure and Design, Department of Chemistry, University of Georgia, Athens, Georgia 30602-2556Search for more papers by this author First published: April 1996 https://doi.org/10.1002/(SICI)1096-987X(199604)17:5/6 3.0.CO;2-SCitations: 36 † This article includes Supplementary Material available from the authors upon request AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Abstract The MM4 force field has been extended to alkenes. It retains most of the formalism and computational schemes that were present in MM3. Several additional cross-terms have been added in MM4 that were not present in MM3, mainly to improve vibrational frequencies but also to improve structures and energies. About 100 molecules have been examined, many in multiple conformations. Geometries are fit for the most part to within the following ranges: 0.004 Å for bond lengths, 1° for bond angles, 4° for torsion angles, and 0.5% for moments of inertia (r2). Conformational energy differences/barriers are generally fit to within 0.5 kcal/mol unless they are very large. The vibrational frequency rms error for 7 alkenes is 25 cm−1. © 1996 by John Wiley & Sons, Inc. References 1(a) N. L. Allinger, Y. H. Yuh, and J.-H. Lii, J. Am. Chem. Soc., 111, 8551 (1989); (b) J.-H. Lii and N. L. Allinger, J. Am. Chem. Soc., 111, 8566 (1989); (c) J.-H. Lii and N. L. Allinger, J. Am. Chem. Soc., 111, 8576 (1989). 2 N. L. Allinger, F. Li, and L. Yan, J. Comput. Chem., 11, 848 (1990). 3 N. L. Allinger, F. Li, L. Yan, and J. C. Tai, J. Comput. Chem., 11, 868 (1990). 4(a) J. H. Schachtschneider and R. G. Snyder, Spectrochim. Acta, 19, 117 (1963); (b) R. G. Snyder and J. H. Schachtschneider, Spectrochim. Acta, 21, 169 (1965). 5 Previous article on alkanes; N. L. Allinger, K. Chen, and J.-H. Lii. 6(a) N. L. Allinger, M. Rahman, and J.-H. Lii, J. Am. Chem. Soc., 112, 8293 (1990); (b) L. R. Schmitz and N. L. Allinger, J. Am. Chem. Soc., 112, 8307 (1990), and later articles. 7(a) N. Nevins and N. L. Allinger, "Molecular Mechanics (MM4) Calculations on Conjugated Hydrocarbons," following article; (b) N. Nevins and N. L. Allinger, "Molecular Mechanics (MM4) Vibrational Frequency Calculations for Alkenes and Conjugated Hydrocarbon Systems," second following article. 8(a) L. S. Bartell, J. Am. Chem. Soc., 99, 3279 (1977); (b) N. L. Allinger, J. Am. Chem. Soc., 99, 8127 (1977). 9 L. Yan, Ph.D. dissertation, University of Georgia, August 1991. 10 R. Wallace and J. P. Leroy, Chem. Phys., 144, 371 (1990). 11 U. Burkert and N. L. Allinger, Molecular Mechanics, American Chemical Society, Washington, DC, 1982, p. 28. 12 C. J. Böttcher, Theory of Electric Polarization, Elsevier, Amsterdam, 1952. 13 S. J. Weiner, P. A. Kollman, D. A. Case, U. C. Singh, C. Ghio, G. Alagona, S. Profeta, Jr., and P. Weiner, J. Am. Chem. Soc., 106, 765 (1984). 14(a) B. R. Brooks and H. F. Schaefer, III, J. Am. Chem. Soc., 101, 307 (1979); (b) H. Ichikawa, Y. Ebisawa, and A. Shigihara, Bull. Chem. Soc. Jpn., 58, 3619 (1985). 15 R. Grev, personal communication. 16 U. Dinur and A. T. Hagler, J. Am. Chem. Soc., 111, 5149 (1989). 17 T. A. Halgren, J. Am. Chem. Soc., 114, 7827 (1992). 18 N. L. Allinger and J.-H. Lii, J. Comput. Chem., 8, 1146 (1987). 19 A. L. McClellan, Tables of Experimental Dipole Moments, Vol. 2, 1974. 20 L. S. Bartell, E. A. Roth, C. D. Hollowell, K. Kuchitsu, and J. E. Young, Jr., J. Chem. Phys., 42, 2683 (1965). 21 I. Tokue, T. Fukuyama, and K. Kuchitsu, J. Mol. Struct., 17, 207 (1973). 22(a) S. Kondo, E. Hirota, and Y. Morino, J. Mol. Spectr., 28, 471 (1968); (b) D. V. Hemelrijk, L. V. der Enden, H. J. Geise, H. L. Seller, and L. Schäfer, J. Am. Chem. Soc., 102, 2189 (1980). 23 A. Almenningen, I. M. Anfinsen, and A. Haaland, Acta. Chem. Scand., 24, 43 (1970). 24(a) I. Tokue, T. Fukuyama, and K. Kuchitsu, J. Mol. Struct., 23, 33 (1974); (b) L. H. Scharpen and V. W. Laurie, J. Chem. Phys., 39, 1732 (1963). 25 J. H. M. Ter Brake, J. Mol. Struct., 118, 63 (1984). 26 J. H. M. Ter Brake and F. C. Mijlhoff, J. Mol. Struct., 77, 253 (1981). 27 L. Doms, L. van den Enden, and H. J. Geise, J. Mol. Struct., 94, 241 (1983). 28 T. Shimanouchi, Y. Abe, and K. Kuchitsu, J. Mol. Struct., 2, 82 (1968). 29 S. Saebø and J. E. Boggs, J. Mol. Struct., 73, 137 (1981). 30 M. Traetteberg, Acta. Chem. Scand., B29, 29 (1975). 31 O. Ermer and S. A. Mason, Acta. Cryst., B38, 2200 (1982). 32 G. Dallinga and L. H. Toneman, J. Mol. Struct., 1, 117 (1967). 33 H. Oberhammer and S. H. Bauer, J. Am. Chem. Soc., 73, 137 (1951). 34 J. H. M. Ter Brake, J. Mol. Struct., 118, 73 (1984). 35 M. I. Davis and T. W. Muecke, J. Phys. Chem., 74, 1104 (1970). 36 J. F. Chiang, R. Chiang, K. C. Lu, E.-M. Sung, and M. D. Harmony, J. Mol. Struct., 41, 67 (1977). 37 A. Yokozeki and K. Kuchitsu, Bull. Chem. Soc. Jpn., 44, 2356 (1971). 38 G. Knuchel, G. Grassi, B. Vogelsanger, and A. Bauder, J. Am. Chem. Soc., 115, 10845 (1993). 39 S. Yamamoto, M. Nakata, T. Fukuyama, K. Kuchitsu, D. Hasselmann, and O. Ermer, J. Phys. Chem., 86, 529 (1982). 40 A. Yokozeki and K. Kuchitsu, Bull. Chem. Soc. Jpn., 44, 1783 (1971). 41 M. Nakata, S. Yamamoto, T. Fukuyama, and K. Kuchitsu, J. Mol. Struct., 100, 143, (1983). 42 D. R. Lide, Jr., and D. Christensen, J. Chem. Phys., 35, 1374 (1961). 43 S. Kondo, Y. Sakurai, E. Hirota, and Y. Morino, J. Mol. Spectr., 34, 231 (1970). 44 L. H. Scharpen and V. W. Laurie, J. Chem. Phys., 39, 1732 (1963). 45 R. A. Creswell, M. Pagitsas, P. Shoja-Chaghervand, and R. H. Schwendeman, J. Phys. Chem., 83, 1427 (1979). 46 L. H. Scharpen, J. E. Wollrab, and D. P. Ames, J. Chem. Phys., 49, 2368 (1968). 47 G. W. Rathjens, Jr., J. Chem. Phys., 36, 2401 (1962). 48 F. Li, Ph.D. dissertation, Department of Chemistry, University of Georgia, 1987. 49 E. Hirota, J. Chem. Phys., 45, 1984 (1966). 50 J. E. Kilpatrick and K. S. Pitzer, J. Res. Natl. Bur. Std., 37, 163 (1949). 51(a) T. N. Sarachman, J. Chem. Phys., 49, 3146 (1968); (b) S. Kondo, Y. Sakurai, E. Hirota, and Y. Morino, J. Mol. Spec., 34, 231 (1970). 52 J. R. Durig, C. W. Hawley, and J. Bragin, J. Chem. Phys., 57, 1426 (1972). 53 V. W. Laurie, J. Chem. Phys., 34, 1516 (1961). 54 D. W. Scott, H. L. Finke, J. P. McCullough, M. E. Gross, J. F. Messerly, R. E. Pennington, and G. Waddington, J. Am. Chem. Soc., 77, 4993 (1955). 55 J. Laane and R. C. Lord, J. Chem. Phys., 47, 4941 (1967). 56 J. Saltiel and J. L. Charlton, In Rearrangements in the Ground and Excited States, Vol. 3, P. Demayo, Ed., Academic, New York, 1980, p. 25. 57 J. E. Gano, D. Lenoir, B.-S. Park, and R. A. Roesner, J. Org. Chem., 52, 5636 (1987). 58 G. Trinquier and J.-P. Malrieu, Chem. Phys. Lett., 72, 328 (1980). 59(a) N. L. Allinger, R. S. Grev, B. F. Yates, and H. F. Schaefer, III, J. Am. Chem. Soc., 112, 114 (1990); (b) W. Allen, unpublished work. 60 K. B. Wiberg and E. Martin, J. Am. Chem. Soc., 107, 5035 (1985). 61 I. Pettersson and K. Gundertofte, J. Comput. Chem., 12, 839 (1991). 62 S. Kondo, E. Hirota, and Y. Morino, J. Mol. Spectr., 28, 471 (1968). 63 D. V. Hemelrijk, L. van den Enden, H. J. Geise, H. L. Sellers, and L. Schafer, J. Am. Chem. Soc., 102, 2189 (1980). 64 A. J. Barnes and J. D. R. Howells, J. Chem. Soc., Faraday Trans., 69, 532 (1973). 65 J. R. Durig and D. A. C. Compton, J. Phys. Chem., 84, 773 (1980). 66 J. R. Durig and D. J. Gerson, J. Phys. Chem., 85, 426 (1981). 67 R. A. Creswell, M. Pagitsas, P. Shojachaghervand, and R. Schwendeman, J. Phys. Chem., 83, 1427 (1979). 68 F. H. A. Rummens, C. Simon, C. Coupry, and N. Lumbroso-Bader, Org. Magn. Reson., 13, 33 (1980). 69 W. D. Allen, A. G. Csaszar, and D. A. Horner, J. Am. Chem. Soc., 114, 6834 (1992). 70 V. E. Rivera-Gaines, S. J. Leibowitz, and J. Laane, J. Am. Chem. Soc., 113, 9735 (1991). 71 F. A. L. Anet, D. I. Freedberg, J. W. Storer, and K. N. Houk, J. Am. Chem. Soc., 114, 10969 (1992). 72 T. L. Smithson and H. J. Wieser, J. Chem. Phys., 72, 2340 (1980). 73 J. R. Durig, R. O. Carter, and L. A. Carreira, J. Chem. Phys., 60, 3098 (1974). 74 Y. Inoue, T. Ueoka, T. Kuroda, and T. Hakushi, J. Chem. Soc. Chem. Commun., 1031 (1981). 75 A. C. Cope and B. A. Pawson, J. Am. Chem. Soc., 87, 3649 (1965). 76 D. W. Rogers, H. von Voithenberg, and N. L. Allinger, J. Org Chem., 43, 360 (1978). 77 J. Laane and R. C. Lord, J. Mol. Spectr., 39, 340 (1971). 78 Gaussian92/DFT, Revision F.2, M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. W. Wong, J. B. Foresman, M. A. Robb, M. Head-Gordon, E. S. Replogle, R. Gomperts, J. L. Andres, K. Raghavachari, J. S. Binkley, C. Gonzalez, R. L. Martin, D. J. Fox, D. J. Defrees, J. Baker, J. J. P. Stewart, and J. A. Pople, Gaussian, Inc., Pittsburgh, PA, 1993. Citing Literature Volume17, Issue5-6April 1996Pages 669-694 ReferencesRelatedInformation