GAS-PHASE ACIDITIES OF ACROLEIN AND METHYL ACRYLATE

被引：5

作者：

BERNASCONI, CF ^{[1
]}

STRONACH, MW ^{[1
]}

DEPUY, CH ^{[1
]}

GRONERT, S ^{[1
]}

机构：

[1] UNIV COLORADO,DEPT CHEM & BIOCHEM,BOULDER,CO 80309

来源：

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY | 1990年 / 3卷 / 05期

关键词：

D O I：

10.1002/poc.610030512

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Gas‐phase acidities of acrolein and methyl acrylate were measured by bracketing in a flowing afterglow/SIFT apparatus. For acrolein ΔG°acid = 369 ± 4 kcal mol−1 and for methyl acrylate ΔG°acid = 373 ± 4 kcal mol−1. These acidities are substantially lower than those of the saturated analogs propionaldehyde and methyl acetate, respectively, even though hydrogens attached to sp2‐hybridized carbon are intrinsically more acidic than those attached to sp3‐hybridized carbon. Resonance stabilization of the neutral form by conjugation of the CC double bond with the carbonyl group and allenic destabilization of the anionic form of the two acids can account for the relatively low acidities. Copyright © 1990 John Wiley & Sons Ltd.

引用

页码：346 / 348

页数：3

共 18 条

[1]

Bartmess J. E., 1979, GAS PHASE ION CHEM, V2, P87

[2] SCALE OF ACIDITIES IN THE GAS-PHASE FROM METHANOL TO PHENOL [J].