Conformational behaviour of hydroxamic acids: ab initio and structural studies

被引：64

作者：

Brown, DA ^{[1
]}

Coogan, RA ^{[1
]}

Fitzpatrick, NJ ^{[1
]}

Glass, WK ^{[1
]}

Abukshima, DE ^{[1
]}

Shiels, L ^{[1
]}

Ahlgren, M ^{[1
]}

Smolander, K ^{[1
]}

Pakkanen, TT ^{[1
]}

Pakkanen, TA ^{[1
]}

Perakyla, M ^{[1
]}

机构：

[1] UNIV JOENSUU,DEPT CHEM,FIN-80101 JOENSUU,FINLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1996年 / 12期

关键词：

D O I：

10.1039/p29960002673

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The conformational behaviour of a series of monohydroxamic acids, p-RC(6)H(4)CONR'OH (R = Me, R' = H, Me; R = MeO, R' = H, Me; R = NO2, R' = H), and a series of dihydroxamic acids, (CH2)(n)(CONR'OH)(2) (n = 3-8, 10, R' = H and n = 7, R' = Me), in methanol, DMSO and chloroform and in the solid state has been examined using IR and NMR spectroscopy, X-Ray crystal structure determinations of p-MeC(6)H(4)CONMeOH and the monohydrate of glutarodihydroxamic acid (n = 3) together with ab initio molecular orbital calculations for several hydrated and unhydrated hydroxamic acids have been performed. Hydrogen bonding effects are shown to be important in both the solid state and solution, The cis(Z) conformation of the hydroxamate group(s) (CONHOH) is preferentially stabilized by hydrogen bonding with water molecules.

引用

页码：2673 / 2679

页数：7

共 22 条

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BLATT AH, 1963, ORGANIC SYNTHESES, V4

[2]

BRECHER BH, 1970, ACTA CRYSTALLOGR B, V26, P1705

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