1. Molecular mechanics calculations |
81 |
IV. ACKNOWLEDGMENT
We are grateful to Prof. Norman L. Allinger for his most valuable discussion and comments.
V.REFERENCES
1.(a) U. Burkert and N. L. Allinger, Molecular Mechanics, ACS Monograph 177, American Chemical Society, Washington D.C., 1982.
(b)D. B. Boyd and K. B. Lipkowitz, J. Chem. Educ., 59, 269 (1982).
(c)E. M. Engler, J. D. Andose and P. v. R. Schleyer, J. Am. Chem. Soc., 95, 8005 (1973).
(d)C. Altona and D. H. Faber, Top. Curr. Chem., 45, 1 (1974).
(e)L. S. Bartell, J. Am. Chem. Soc., 99, 3279 (1977).
(f)S. R. Niketic and K. Rasmussen, The Consistent Force Field, Springer-Verlag, Berlin, 1977.
(g)E. Osawa and H. Musso, Top. Stereochem., 13, 117 (1982).
2.(a) S. J. Weiner, P. A. Kollman, D. A. Case, U. C. Singh, C. Chio, G. Alagona, S. Profeta and P. Weiner, J. Am. Chem. Soc., 106, 765 (1984).
(b)S. J. Weiner, P. A. Kollman, D. T. Nguyen and D. A. Case, J. Comput. Chem., 7, 230 (1986).
3.(a) N. L. Allinger, J. Am. Chem. Soc., 99, 8127 (1977).
(b)N. L. Allinger and Y. Yuh, QCPE, 12, 395 (1980).
(c)MM2: N. L. Allinger, Y. H. Yuh and S. Profeta, Program No. 406 Quantum Chemistry Program Exchange, Indiana University, Bloomington, Ind.
(d)MM2: N. L. Allinger, Y. H. Yuh and S. Profeta, MM2-87, Quantum Chemistry Program Exchange, Indiana University, Bloomington, Ind.
4.(a) N. L. Allinger, Y. Yuh and J. -H. Lii, J. Am. Chem. Soc., 111, 8551 (1989).
(b)MM3: Available from the Quantum Chemistry Program Exchange, Indiana University, Bloomington, IN and Tripos Associates, 1699 Hanley Road, St. Louis, MI 63144.
5.S. Profeta Jr. and N. L. Allinger, J. Am. Chem. Soc., 107, 1907 (1985).
6.L. R. Schmitz, and N. L. Allinger, J. Am. Chem. Soc., 112, 8307 (1990).
7.C. Jaime and E. Osawa, Tetrahedron, 39, 2769 (1983).
8.N. L. Allinger, M. R. Imam, M. R. Frierson, Y. H. Yuh and L. Schafer, in Mathematics and Computational Concepts in Chemistry, (Ed. N. Trinajstic), Eis Horwood, London, 1986.
9.A. D. Buckingham and B. D. Utting, Annu. Rev. Phys. Chem., 21, 287 (1970).
10.J. M. Leonard and W. P. Ashman, J. Comput. Chem., 11, 230 (1990).
11.K. Takagi and T. Kojima, J. Phys. Soc. Jpn., 30, 1145 (1971).
12.B. Beagley and A. R. Medwid, J. Mol. Struct., 38, 229 (1977).
13.L. A. Carreira and R. C. Lord, J. Chem. Phys., 51, 2735 (1969).
14.(a) V. S. Mastryukov, O. V. Dorofeeva, L. V. Vilkov and I. Hargittai, J. Mol. Struct., 34, 99 (1976).
(b)O. V. Dorofeeva, V. S. Mastryukov and L. V. Vilkov, J. Chem. Soc. Chem. Commun., 772 (1973).
15.K. Tanabe, S. Tsuzuki, T. Uchimaru and E. Osawa, Chemistry Express, 3, 367 (1988).
16.D. Delpeyroux, B. Blaive and R. Gallo, Propellants, Explosives, Pyrotechnics, 19, 70 (1994).
17.T. Polonski, M. J. Milewska and A. Katrusiak, J. Am. Chem. Soc., 115, 11410 (1993).
18.J. Kao and D. Leister, J. Am. Chem. Soc., 110, 7286 (1988).
19.A. J. Hopfinger and R. A. Pearlstein, J. Comput. Chem., 5, 486 (1984).
20.H. Kooijman, J. A. Kanters and J. Kroon, Acta Crystallogr., B49, 356 (1993).
21.D. -A. Wang, S. -S. Li and H. -M. Xiao, Acta Chimica Sinica, 50, 335 (1992).
22.(a) P. Aped, B. Fuchs, L. Schleifer and S. Wolfe, J. Comput. Chem., 10, 265 (1989).
(b)H. Senderowitz, P. Aped and B. Fuchs, Tetrahedron, 48, 1131 (1992).
23.(a) A. J. Kirby, The Anomeric Effect and Related Stereoelectronic Effects on Oxygen, SpringerVerlag, Berlin, 1983.
(b)W. A. Szarek and D. Horton (Eds.), Anomeric Effect. Origins and Consequences, ACS Symposium Series 87, Washington D.C., 1979.
(c)P. Deslongchamps, Stereoelectronic Effects in Organic Chemistry, Wiley, New York, 1983.
(d)G. R. J. Thatcher (Ed.) The Anomeric Effect and Associated Stereoelectronic Effects, ACS Symposium Series 539, Washington D.C., 1992.
(e)E. Juaristi and G. Cuevas, The Anomeric Effect, CRC Press, Boca Laten. Fl., Inc. 1995.
82 |
Pinchas Aped and Hanoch Senderowitz |
24.(a) T. A. Crabb and A. R. Katritzky, Adv. Heterocycl. Chem., 36, 1 (1983).
(b)S. Wolfe, M. H. Wangbo and D. J. Mitchell, Carbohydr. Res., 69, 1 (1979).
25.(a) C. Altona, Ph.D. Thesis, University of Leiden, 1964.
(b)C. Romers, C. Altona, H. R. Buys and E. Havinga, Top. Stereochem., 4, 39 (1969).
26.(a) L. Norskov-Lauritsen and N. L. Allinger, J. Comput. Chem., 5, 326 (1984).
(b)P. Aped, Y. Apeloig, A. Ellencweig, B. Fuchs, I. Goldberg, M. Karni and E. Tartakovsky, J. Am. Chem. Soc., 109, 1486 (1987).
(c)P. Aped, B. Fuchs, I. Goldberg, H. Senderowitz, E. Tartakovsky and S. Weinman, J. Am. Chem. Soc., 114, 5585 (1992).
(d)H. Senderowitz and B. Fuchs, J. Mol. Struct. THEOCHEM, invited article, in press.
(e)B. Fernandez,´ M. A. Rios and L. Carballeira, J. Comput. Chem., 12, 78 (1991).
27.H. Senderowitz, P. Aped, and B. Fuchs, Helv. Chim. Acta, 73, 2113 (1990).
28.H. Senderowitz, P. Aped and B. Fuchs, J. Comput. Chem., 14, 944 (1993).
29.H. Senderowitz, P. Aped and B. Fuchs, Tetrahedron, 49, 3879 (1992).
30.(a) N. L. Allinger, R. A. Kok and M. R. Iman, J. Comput. Chem., 9, 591 (1988).
(b)J. -H. Lii and N. L. Allinger, J. Phys. Org. Chem., 7, 591 (1994).
31.H. D. Thomas, K. Chen and N. L. Allinger, J. Am. Chem. Soc., 116, 5887 (1994).
32.Y. Hamada, M. Tsuboi, K. Yamanouchi and K. Kuchitsu, J. Mol. Struct., 146, 253 (1986).
33.J. D. Swalen and J. Ibers, J. Chem. Phys., 36, 1914 (1962).
34.L. R. Schmitz, N. L. Allinger and S. Profeta Jr., J. Comput. Chem., 9, 460 (1988).
35.N. L. Allinger, U. Burkert and S. Profeta Jr., J. Comput. Chem., 1, 281 (1980).
36.C. Van Alsenoy, K. Siam, J. D. Ewbank and L. Schafer, J. Mol. Struct. THEOCHEM, 136, 77 (1986).
37.D. Cremer, O. V. Dorofeeva and V. S. Mastryukov, J. Mol. Struct., 75, 225 (1981).
38.H. Gunther, G. Schrem and H. Oberhammer, J. Mol. Spectrosc., 104, 152 (1984).
39.G. Pfafferot, H. Oberhammer, J. E. Boggs and W. Caminati, J. Am. Chem. Soc., 107, 2305 (1985).
40.G. Pfafferot, H. Oberhammer and J. E. Boggs, J. Am. Chem. Soc., 107, 2309 (1985).
41.Z. Latajka and S. Scheiner, J. Comput. Chem., 8, 674 (1987).
42.N. L. Allinger, L. R. Schmitz, I. Motoc, C. Bender and J. K. Labanowski, J. Phys. Org. Chem., 3, 732 (1990).
43.N. L. Allinger, J. Kuang and H. D. Thomas, J. Mol. Struct. THEOCHEM, 209, 125 (1990).
44.N. L. Allinger, L. Yan and K. Chen, J. Comput. Chem., 15, 1321 (1994).
45.Y. Koga and S. Kondo, J. Mol. Spectrosc., 105, 93, (1984).
46.Y. Amatatsu, K, Hamada and M. Tsuboi, J. Mol. Spectrosc., 111, 29 (1985).
47.Selected values of electric dipole moments for molecules in the gas phase, National Standard
Reference Data National Bureau of Standards, 10 (1967).
48.MP2 methods at the 6-31GŁ level using the GAUSSIAN90 program, See W. J. Hehre, L. Radom,
P.v. R. Schleyer and J. A. Pople, Ab initio Molecular Orbital Theory, Wiley, New York, 1986.
49.J. C. Evans, Spectrochim. Acta, 16, 428 (1960).
50.R. A. Kydd and A. R. C. Dunham, J. Mol. Struct., 98, 39 (1983).
51.R. Meyer, Helv. Chim. Acta, 61, 1418 (1978).
52.M. Clark, R. D. Cramer III and N. Van Opdenbosch, J. Comput. Chem., 10, 982 (1989).
53.Tripos Associates, 1699 S. Hanley Road, Suite 303, St. Louis, MO, 63144, SYBYL 5.2 (1988).
54.J. P. Lowe, Prog. Phys. Org. Chem., 6, 1 (1968).
55.N. C. Franklin and H. Feltkamp, Tetrahedron, 22, 2801 (1966).
56.F. H. Allen, S. Bellard, M. D. Brice, B. A. Cartwright, A. Doubleday, H. Higgs, T. Hummelink,
B.G. Hummelink-Peters, O. Kennard, W. D. S. Motherwell, J. R. Rodgers and D. G. Watson,
Acta Crystallogr., 35, 2331 (1979).
57.S. L. Mayo, B. D. Olafson and W. A. Goddard III, J. Phys. Chem., 94, 8897 (1990).
58.A. K. Rappe, C. J. Casewit, K. S. Colwell, W. A. Goddard III and W. M. Skiff, J. Am. Chem. Soc., 114, 10024 (1992).
59.C. J. Casewit, K. S. Colwell and A. K. Rappe, J. Am. Chem. Soc., 114, 10035 (1992).
60.K. Gundertofte, T. Liljerors, P. -O. Norrby, and I. Pettersson, J. Comput. Chem., 17, 429 (1996).
61.MacMimic/MM2(91), InStar Software AB, IDEON Research Park, S-223 70 Lund, Sweden.
62.InStar Software AB, IDEON Research Park, S-223 70 Lund Sweden.
63.F. Mohamadi, N. G. J. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang,
T.Hendrickson and W. C. Still, J. Comput. Chem., 11, 440 (1990).
1. Molecular mechanics calculations |
83 |
64.Cerius2 is available from Molecular Simulations Inc., 16 New England Executive Park, Burlington, MA 01803.
65.Alchemy III, Tripos Associates Inc., 1699 South Hanley Road, Suite 303, St. Louis, Missouri 63144.
66.J. E. Anderson, D. Casarini and L. Lunazzi, J. Chem. Soc., Perkin Trans. 2, 11, 1791 (1990).
67.(a) A. M. Belostotskii, H. E. Gottlieb, P. Aped and A. Hassner, submitted for publication.
(b)A. M. Belostotskii, P. Aped and A. Hassner, THEOCHEM, submitted.
(c)C. H. Bushweller, W. G. Anderson, P. E. Stevenson, D. L. Burkey and I. W. O’Neil, J. Am. Chem. Soc., 96, 3892 (1974).
68.M. R. Whalon, J. G. Brennan, R. P. Marcantonio and R. P. Domingue, J. Am. Chem. Soc., 104, 6224 (1982).
69.D. R. Lide Jr. and D. E. Mann, J. Chem. Phys., 28, 572 (1958).
70.S. H. Fleischman, M. R. Whalon, C. D. Rithner, G. L. Grady and C. H. Bushweller, Tetrahedron Lett., 23, 4233 (1982).
71.C. T. Danehey Jr., G. L. Grady, P. R. Bonneau and C. H. Bushweller, J. Am. Chem. Soc., 110, 7269 (1988).
72.J. H. Brown and C. H. Bushweller, J. Am. Chem. Soc., 114, 8153 (1992).
73.J. H. Brown and C. H. Bushweller, J. Phys. Chem., 98, 11411 (1994).
74.J. E. Anderson, D. Casarini and L. Lunazzi, J. Chem. Soc. Perkin Trans. 2, 1431 (1991).
75.S. Davalli, L. Lunazzi and D. Macciantelli, J. Org. Chem., 56, 1739 (1991).
76.L. Lunazzi, C. Magagnoli, M. Guerra and D. Macciantelli, Tetrahedron Lett., 3031 (1979).
77.A. G. Giumanini, G. Verardo, S. Bruckner, L. Malpezzi and G. Cerioni, J. Mol. Struct., 323, 139 (1994).
78.M. Cygler, T. Markowicz, J. Skolimowski and R. Skowronski, J. Mol. Struct., 68, 161 (1980).
79.A. M. Belostotskii, H. E. Gottlieb and A. Hassner, J. Am. Chem. Soc., in press.
80.(a) S. F. Nelsen, J. T. Ippoliti, T. B. Frigo and P. A. Petillo, J. Am. Chem. Soc., 111, 1776 (1989).
(b)S. F. Nelsen, D. J. Steffek, G. T. Cunkle and P. M. Gannett, J. Am. Chem. Soc., 104, 6641 (1982).
(c)S. F. Nelsen, G. R. Weisman, E. L. Clennan and V. E. Peacock, J. Am. Chem. Soc., 98, 6893 (1976).
(d)S. F. Nelsen and G. R. Weisman, J. Am. Chem. Soc., 98, 1842 (1976).
(e)J. W. Davies, J. R. Malpass and R. E. Moss, Tetrahedron Lett., 26, 4533 (1985).
81.K. Rasmussen and C. Tosi, Acta Chem. Scand. Ser. A, A37, 79 (1983).
82.L. Carballeira, R. A. Mosquera, M. A. Rios and C. A. Tovar, J. Mol. Struct., 193, 263 (1989).
83.K. M. Marstokk and H. Mollendal, J. Mol. Struct., 49, 221 (1978).
84.(a) A. Yokozeki and K. Kuchitsu, Bull. Chem. Soc. Jpn., 44, 2926 (1971).
(b)A. Yokozeki and K. Kuchitsu, Bull. Chem. Soc. Jpn., 43, 2664 (1970).
85.C. Van Alsenoy, K. Siam, J. D. Ewbank and L. Schafer, J. Mol. Struct. THEOCHEM, 136, 77 (1986).
86.N. L. Allinger, J. G. D. Carpenter and F. M. Karkowski, J. Am. Chem. Soc., 87, 1232 (1965).
87.V. M. Gittins, P. J. Heywood and E. Wyn-Jones, J. Chem. Soc. Perkin Trans. 2, 1642 (1976).
88.K. Fukushima, Bull. Chem. Soc. Jpn., 52, 2871 (1979).
89.A. R. Katritzky, V. J. Baker, F. M. S. Brito-Palma, I. J. Ferguson and L. Anghoni, J. Chem. Soc. Perkin Trans. 2, 1746 (1980).
90.(a) R. G. Lett, L. Petrakis, A. F. Ellis and R. K. Jensen, J. Phys. Chem., 74, 2816 (1970).
(b)R. K. Harris and R. A. Spragg, J. Chem. Soc., Chem. Commun., 314 (1966).
(c)J. L. Sdmeier and G. Occupati, J. Am. Chem. Soc., 90, 154 (1968).
91.T. G. Momchilova and P. M. Ivanov, J. Mol. Struct. THEOCHEM, 107, 133 (1993).
92.C. A. G. Hassnoot, F. A. A. M. De Leeuw and C. Altona, Tetrahedron, 36, 2783 (1980).
93.R. Cini, G. Giorgi, D. Masi, A. Sabatini and A. Vacca, J. Chem. Soc. Perkin Trans. 2, 765 (1991).
94.T. W. Hambley, C. J. Hawkins, J. A. Palmer and M. R. Snow, Aust. J. Chem., 34, 45 (1981).
95.R. D. Hancock and G. J. McDougall, Adv. Mol. Relaxation Interact. Processes, 18, 99 (1980).
96.G. J. McDougall, R. D. Hancock and J. C. A. Boeyens, J. Chem. Soc. Dalton, Trans., 1438 (1978).
97.J. C. A. Boeyens, G. J. McDougall and R. D. Hancock, S. Afr. J. Chem., 32, 23 (1979).
98.N. L. Allinger, Adv. Phys. Org. Chem., 13, 1 (1976).
99.P. G. Potvin and M. H. Wong, Can. J. Chem., 66, 2914 (1988).
84 |
Pinchas Aped and Hanoch Senderowitz |
100.M. G. B. Drew, D. Marrs, J. Hunter and J. Nelson, J. Chem. Soc., Dalton Trans., 11 (1992).
101.M. A. Santos and M. G. B. Drew, J. Chem. Soc., Faraday Trans., 87, 1321 (1991).
102. MM2MX program contained with the RIPS program QCPE No. 588: D. M. Ferguson and D. J. Raber, Quantum Chemistry Program Exchange, Chemistry Department, Indiana University, IN, QCPE 395, and based on N. L. Allinger and Y. H. Yuh, MM2-77, 1989.
103.(a) G. Wipff, P. Weiner and P. A. Kollman, J. Am. Chem. Soc., 104, 3249 (1982).
(b)A. E. Howard, U. C. Singh, M. Billeter and P. A. Kollman, J. Am. Chem. Soc., 110, 6984 (1988).
(c)M. J. Bovill, D. J. Chadwick, I. O. Sutherland and D. Watkin, J. Chem. Soc., Perkin Trans. 2, 1529 (1980).
(d)J. R. Damewood, W. D. Anderson and J. J. Urban, J. Comput. Chem., 9, 111 (1988).
104.D. Maverick, P. Seiler, W. B. Schweizer and J. D. Dunitz, Acta Crystallogr., Sect. B, 36, 615 (1980).
105.A. Espinosa, M. A. Gallo, A. Entrena and J. A. Gomez, J. Mol. Struct., 326, 249 (1994).
106.D. Kocjan and D. D. Hadzi, J. Pharm. Pharmacol., 35, 780 (1983).
107.A. M. Johansson, J. L. G. Nilsson, A. Karlen, U. Hacksell, K. Svensson, A. Carlsson, L. Kenne and S. Sundell, J. Med. Chem., 30, 1135 (1987).
108.H. Wikstrom, J-H. Lii and N. L. Allinger, J. Med. Chem., 30, 1115 (1987).
109.T. Liljefors and K. P. Boegesoe, J. Med. Chem., 31, 306 (1988).
110.(a) T. J. Petcher, J. Schmutz, H. P. Weber and T. G. White, Experentia, 31, 1390 (1975).
(b)A. Jaunin, T. J. Petcher and H. P. Weber, J. Chem. Soc. Perkin Trans. 2, 186 (1977).
111.R. W. Alder, R. J. Arrowsmith, A. Casson, R. B. Sessions, E. Heilbronner, B. Kovac, H. Huber and M. Taagepera, J. Am. Chem. Soc., 103, 6137 (1981).
112.R. W. Alder, Chem. Rev., 89, 1215 (1989).
113.M. E. Jason and P. R. Kurzweil, J. Org. Chem., 56, 3664 (1991).
114.S. Li and N. L. Allinger, Tetrahedron, 44, 1335 (1988).
115.Serena Software, Box 3076, Bloomington, IN, 47402-3076.
116.T. Polonski and M. J. Milewska, Tetrahedron Lett., 32, 3255 (1991).
117.(a) W. J. Colucci, S. J. Jungk and R. D. Gandour, Magn. Reson. Chem., 23, 335 (1985).
(b)W. J. Colucci, R. D. Gandour and E. A. Mooberry, J. Am. Chem. Soc., 108, 7141 (1986).
118.T. Polonski and K. Prajer, Tetrahedron, 32, 847 (1976).
119.G. Cerioni, J. Phys. Org. Chem., 4, 260 (1991).
120.D. W. Boykin, G. H. Deadwyler and A. L. Baumstark, Magn. Reson. Chem., 26, 19 (1988).
121.W. Caminati and A. G. Giumanini, J. Mol. Struct., 162, 255 (1987).
122.(a) Y. -D. Wu and K. N. Houk, J. Am. Chem. Soc., 109, 908 (1987).
(b)D. C. Spellmeyer and K. N. Houk, J. Org. Chem., 52, 959 (1987).
123.K. Rudolf, J. M. Hawkins, R. J. Loncharich and K. N. Houk, J. Org. Chem., 53, 3879 (1988).
124.B. E. Maryanoff and H. R. Almond Jr., J. Org. Chem., 51, 3295 (1986).
125.F. A. L. Anet and J. Krane, Isr. J. Chem., 20, 72 (1980).
126.A. Miller and G. Procter, Tetrahedron Lett., 31, 1041 (1990).
127.Y. Akutsu, S. Tahara, M. Tamura and T. Yoshida, J. Energ. Mater., 9, 161 (1991).
128.Y. Akutsu and M. Tamura, J. Energ. Mater., 11, 39 (1993).
129.Y. Akutsu, R. Che and M. Tamura, J. Energ. Mater., 11, 195 (1993).
130.W. J. Lauderdale and S. L. Rodgers, Prediction of Molecular Properties, AFAL-TR-87-063 (1987).
131.K. J. Laidler, Can. J. Chem., 34, 626 (1956).
132.A. Bondi, J. Chem. Eng. Data, 8, 371 (1963).
133.S. Bourasseau, J. Energ. Mater., 8, 266 (1990).
134.See Reference 5 of Reference 135.
135.J. R. Holden, Z. Du and H. L. Ammon, J. Comput. Chem., 14, 422-437 (1993).
136.(a) J. P. Ritchie, J. Am. Chem. Soc., 107, 1829 (1985).
(b)J. P. Ritchie and S. M. Bachrach, J. Comput. Chem., 8, 499 (1987).