Molecular structure and conformational analysis of chiral ((-))-3-(4-bromobenzylidene)-1-isopropyl-2-metboxy-4-methylcyclohexede

被引：1

作者：

Shishkin, OV ^{[1
]}

Vashchenko, VV ^{[1
]}

Kutulya, LA ^{[1
]}

Struchkov, YT ^{[1
]}

机构：

[1] NATL ACAD SCI UKRAINE,INST SINGLE CRYSTALS,KHARKOV 310001,UKRAINE

来源：

RUSSIAN CHEMICAL BULLETIN | 1995年 / 44卷 / 12期

关键词：

molecular structure; conformational analysis; crystal structure; X-ray structural analysis; molecular mechanics; ((-))-3-(4-bromobenzylidene)-1-isopropyl-2-methyoxy-4-methylcyclohexene;

D O I：

10.1007/BF00713603

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(-)-3-(4-Bromobenzylidene)-1-isopropyl-2-methoxy-4-methylcyclohexene, capable of inducing spiral supramolecular ordering when introduced to nematic and some smectic mesophases, has been studied by an X-ray structural analysis. The crystals are orthorhombic; at 20 degrees C a = 6.055(1), b = 13.282(3), c = 20.734(4) Angstrom, V = 1668(1) Angstrom(3), d(calc) = 1.380 g cm(-3), space group P2(1)2(1)2(1), Z = 4 The cyclohexene ring has a conformation intermediate between a sofa and a half-chair. The methyl and methoxyl groups are in a syn orientation with respect to the mean plane of the cycle. The angle between the plane of the aryl substituent and the exocyclic double bond is 33 degrees. The observed distortions of bond angles at unsaturated carbon atoms are typical of derivatives of benzylidenecyclohexene. Molecular mechanics calculations demonstrated that the conformation observed in the crystalline state is not the most favorable, and this conformation is stabilized through intermolecular interactions upon stacking in crystals. It was shown that the relative orientation of the methyl and methoxyl groups as well as the orientation of the aryl substituent substantially affect the conformation of the cyclohexene ring.

引用

页码：2331 / 2336

页数：6

共 20 条

[1]

Kulishov V.I., Kutulya L.A., Kuz'min V.E., Kravers M.A., Nemchenok I.B., Stel'makh I.B., Struchkov, Tolochko A.S., Zh. Obshch. Khim., 61, (1991)

[2]

Kulishov V.I., Kutulya L.A., Tolochko A.S., Vashchenko V.V., Yarmolenko S.N., Mitkevich V.V., Tret'yak S.M., Kristallografiya, 36, (1991)

[3]

Kutulya L.A., Kulishov V.I., Tolochko A.S., Yarmolenko S.N., Vashchenko V.V., Novikova I.E., Kristallografiya, 37, (1992)

[4]

Kutulya L.A., Kuznetsov V.P., Lakin E.E., Vashchenko V.V., Patsenker L.D., Kristallografiya, 38, (1993)

[5]

Kutulya L.A., Kuznetsov V.P., Patsenker L.D., Vashchenko V.V., Lakin E.E., Kristallografiya, 39, (1994)

[6]

Kutulya L.A., Nemchenok I.B., Khandrimailova T.V., Kristallografiya, 35, (1990)

[7]

Aliev D.F., Bairamov G.M., Tishchenko V.G., Zh. Fiz. Khim., 61, (1987)

[8]

Gotarelli G., Spada G.P., Mol. Cryst. Liq. Cryst., 123, (1985)

[9]

Kutulya L.A., D. Sc. (Chem.) Thesis, (1992)

[10]

Jackman L.M., Lange B.C., J. Am. Chem. Soc., 103, (1981)

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