N-Benzylideneaniline-like Derivatives and Their Conformation

Abstract

Abstract: To discern the driving force for distorting the geometry of NBA-like species, the relax potential energy scan was performed at the B3LYP/6-311G ^** level, for each molecule of 21 NBA-like species substituted with typical electron donor and/or acceptor at their benzylidene, aniline, and/or imine groups. In general, it is electron interaction, rather than nuclear repulsion between fragments, to distort a molecule away from its planar geometry, and their lowest total electronic energies occur in the geometries with the similar twist angles about 50°. Afterwards, the single point energies for 21 rotational geometries of each of two typical molecules 1 and 17 are calculated by using HF, BLYP, BVWN, B3LYP and MP2 at various Gaussian basis levels. Interestingly, STO-3G is accurate enough to understand the driving force for distorting NBA away from its planar geometry, but it is unreasonable to describe the intra-molecular hydrogen bond.

Key words: Driving force for distorting, Conformation, N-Benzylideneanilines

CLC Number:

O626
O641

TrendMD:

XU Hong, YU Zhong-Heng. N-Benzylideneaniline-like Derivatives and Their Conformation[J]. Chem. J. Chinese Universities, 2005, 26(2): 308.

References

[1] Skrabal P.,Steiger J.,Zollinger H..Helv.Chim.Acta[J],1975,58:800_814 [2] Müller M.,Hohlneicher G..J.Am.Chem.Soc.[J],1990,112:1273_1274 [3] Gould E.S..Mechanismand Structurein Organic Chemistry[M],New York:Holt-Dryden Book Henry Holtand Company,1960:199_250 [4] Burgi H.B.,Dunitz J.D..Helv.Chim.Acta[J],1971,54:1255_1260 [5] Nakai H.,Shiro M.,Ezumi K.et al..Acta Cryst.[J],1976,B 32:1827_1833 [6] Kuze N.,Ebizuka M.,Fujiwara H.et al..J.Phys.Chem.A[J],1998,102:2080_2086 [7] Yu Z.H.,Peng X.Q..J.Phys.Chem.A[J],2001,105:8541_8553 [8] YU Zhong-Heng(虞忠衡),XUAN Zheng-Qian(宣正乾),GUO Yan-Shen(郭彦伸)et al..Chem.J.Chinese Universities(高等学校化学学报)[J],2001,22(1):122_126 [9] Perrin H.,Berges J..J.Mo .lStruct.(Theochem.)[J],1981,76:299_311 [10] Zamir S.,Bernstein J.,Loffe A.et al..J.Chem.Soc.,Perkin Trans.2[J],1994:895_900 [11] Patnail L.N.,Das S..International J.Quantum Chem.[J],1985,27:135_144 [12] Akaba R.,Tokumaru K.,Kobayashi T..Bull.Chem.Soc.Jpn.[J],1980,53:1993_2001 [13] Warren C.H.,Wettermark G.,Weiss K..J.Am.Chem.Soc.[J],1971,93:4658_4663 [14] Giiner V.,Bayari S..Spectrosc.Lett.[J],2002,35(1):83_98 [15] Morley J.O..J.Chem.Soc.,Perkin Trans.2[J],1995:731_734 [16] Ognyanova V.,Andreev G.N.,Stamboliyska B.et al..J.Mo .lStruct.[J],1999,513(1_3):139_148 [17] Morley J.O..J.Mo .lStruct.(Theochem.)[J],1995,340:45_50 [18] Bernstein J..J.Chem.Phys.[J],1981,75(5):2346_2353 [19] Kuze N.,Fujiwara H.,Takeuchi H.et al..J.Phys.Chem.A[J],1999,103(16):3054_3061 [20] Head-Gordon M.,Pople J.A..J.Phys.Chem.[J],1993,97:1147_1151 [21] Burgi H.B.,Dunitz J.D..Helevetica Chim.Acta[J],1970,53:1747_1764 [22] Traetteberg M.,Hilmo L.,Abraham R.J.et al..J.Mo .lStruct.[J],1978,48:395_405 [23] Bally T.,Haselbach E.,Lanyiova S.et al..Helv.Chim.Acta[J],1976,59:486_498 [24] Ebara N..B.Chem.Soc.Jpn.[J],1961,34:1151_1158 [25] Meunier-Piret J.,Germain G.,Declercq J.P.et al..Bul.lSoc.Chim.Belg.[J],1982,91,89_90 [26] Meunier-Piret J.,Germain G.,Declercq J.P.et al..Bul.lSoc.Chim.Belg.[J],1982,91:93_94 [27] Meunier-Piret J.,Piret P.,Germain G.et al..Bul.lSoc.Chim.Belg.[J],1972,81:533_538 [28] Clegg W.,Elsegood M.R.J.,Heath S.L.et al..Acta Crystallogr.[J],1996,C52:2548_2552 [29] Nakai H.,Ezumi K.,Shiro M..Acta Crystallogr.[J],1981,B37:193_197 [30] Yang Q.C.,Tang Y.Q.,Yang W.J.et al..Acta Crystallogr.[J],1998,C54:1532_1534 [31] Destro D.A.,Gavezzotti A.,Simonetta M..Acta Crystallog.[J],1978,B34:2867_2869 [32] Bregman J.,Leiserowitz L.,Schmidt G.M..J.Topochemistry[J],1964:2068_2085 [33] Bregman J.,Leiserowitz L.,Osaki K..Topochemistry[J],1964:2086_2100 [34] Elerman Y.,Elmall A..Acta Crystallogr.[J],1995,C51:2344_2346 [35] Mukherjee A.K.,De R.L.,Ranerjee I.et al..Acta Crystallogr.[J],1999,C55:407_410 [36] KwiatkowskiM.,Kwiatkowski E.,Olechnowicz A.et al..Polish J.Chem.[J],1994,68:85_92 [37] Zhang D.C..Acta Crystallogr.[J],2002,C58:351_352 [38] Surma K.,JaskolskiM.,Kosturkiewicz Z..Acta Crystallogr.[J],1988,C44:1031_1033 [39] Choi C.H.,Kertesz M..J.Phys.Chem.A[J],1997,101(20):3823_3831