Kinetics and mechanism of thermal gas-phase elimination of α and β (N-arylamino)propanoic acid:: experimental and theoretical analysis

被引:14
作者
Al-Awadi, SA [1 ]
Abdallah, MR [1 ]
Hasan, MA [1 ]
Al-Awadi, NA [1 ]
机构
[1] Kuwait Univ, Dept Chem, Safat 13060, Kuwait
关键词
alpha- and beta- (N-arylamino)propanoic acid; thermal gas-phase elimination; theoretical analysis;
D O I
10.1016/j.tet.2004.01.087
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-(N-Phenylamino)propanoic acid la and 3-(N-phenylamino)-propanoic acid 2a together with four of their aryl analogues were pyrolysed in the gas-phase. The reactions were homogeneous and free from catalytic and radical pathways. Analysis of the pyrolysate of 1 showed the elimination products to be carbon monoxide, acetaldehyde and aniline, while the pyrolysate of 2 reveals the formation of acrylic acid in addition to aniline. Theoretical study of the pyrolysis of 2 using an ab initio SCF method lend support to a reaction pathway involving a 4-membered cyclic transition state. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3045 / 3049
页数:5
相关论文
共 17 条
[1]  
Al-Awadi NA, 1999, J PHYS ORG CHEM, V12, P654, DOI 10.1002/(SICI)1099-1395(199908)12:8<654::AID-POC168>3.0.CO
[2]  
2-L
[3]  
Al-Awadi NA, 2000, INT J CHEM KINET, V32, P403, DOI 10.1002/(SICI)1097-4601(2000)32:7<403::AID-KIN2>3.0.CO
[4]  
2-P
[5]  
Al-Awadi NA, 2000, J PHYS ORG CHEM, V13, P499, DOI 10.1002/1099-1395(200009)13:9<499::AID-POC269>3.0.CO
[6]  
2-0
[7]   GAS-PHASE PYROLYTIC REACTIONS - RATE DATA FOR PYROLYSIS OF N-TERT-BUTYLTHIOACETAMIDE AND N-ACETYLTHIOACETAMIDE - ROLE OF POLARITY OF TRANSITION-STATE AND GAMMA-CARBONYL GROUP PROTOPHILICITY [J].
ALAWADI, NA ;
ALBASHIR, RF ;
ELDUSOUQUI, OME .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1989, (06) :579-581
[8]  
AlAwadi NA, 1997, INT J CHEM KINET, V29, P295, DOI 10.1002/(SICI)1097-4601(1997)29:4<295::AID-KIN8>3.0.CO
[9]  
2-P
[10]   THE KINETICS OF MECHANISMS OF METHYL 2-BROMOPROPIONATE AND 2-BROMOPROPIONIC ACID PYROLYSES UNDER MAXIMUM INHIBITION [J].
CHUCHANI, G ;
DOMINGUEZ, RM ;
ROTINOV, A .
INTERNATIONAL JOURNAL OF CHEMICAL KINETICS, 1991, 23 (09) :779-783