Room temperature ionic liquids structure and its effect on the mononuclear rearrangement of heterocycles: An approach using thermodynamic parameters

被引:59
作者
D'Anna, Francesca
Frenna, Vincenzo
Noto, Renato
Pace, Vitalba
Spinelli, Domenico
机构
[1] Univ Palermo, Dipartimento Chim Organ E Paterno, I-90128 Palermo, Italy
[2] Univ Bologna, Dipartimento Chim Organ A Mangini, I-40126 Bologna, Italy
关键词
D O I
10.1021/jo0615549
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The kinetics of the rearrangement of the Z-phenylhydrazone of 3-benzoyl-5-phenyl-1,2,4-oxadiazole (1) into the relevant 4-benzoylamino-2,5-diphenyl-1,2,3-triazole (2) induced by amines have been studied in five room-temperature ionic liquids (RTILs) at different temperatures. The kinetic data collected show that both cationic and anionic parts of RTILs significantly influence the reactivity of the title reaction. The calculated activation parameters allow us to advance hypotheses about the weak interactions operating in RTIL solutions.
引用
收藏
页码:9637 / 9642
页数:6
相关论文
共 65 条
[1]   How polar are room-temperature ionic liquids? [J].
Aki, SNVK ;
Brennecke, JF ;
Samanta, A .
CHEMICAL COMMUNICATIONS, 2001, (05) :413-414
[2]   Mannich-type reaction promoted by an ionic liquid [J].
Akiyama, T ;
Suzuki, A ;
Fuchibe, K .
SYNLETT, 2005, (06) :1024-1026
[3]   Characterizing ionic liquids on the basis of multiple solvation interactions [J].
Anderson, JL ;
Ding, J ;
Welton, T ;
Armstrong, DW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (47) :14247-14254
[4]  
ANSLYN EV, 2004, MODERN PHYS ORGANIC, P643
[5]   Ionic liquids for the convenient synthesis of functional nanoparticles and other inorganic nanostructures [J].
Antonietti, M ;
Kuang, DB ;
Smarsly, B ;
Yong, Z .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (38) :4988-4992
[6]   A STABLE CRYSTALLINE CARBENE [J].
ARDUENGO, AJ ;
HARLOW, RL ;
KLINE, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :361-363
[7]   Examination of ionic liquids and their interaction with molecules, when used as stationary phases in gas chromatography [J].
Armstrong, DW ;
He, LF ;
Liu, YS .
ANALYTICAL CHEMISTRY, 1999, 71 (17) :3873-3876
[8]   Convergent results from experimental and theoretical DFT studies of the intramolecular rearrangement of Z-hydrazones of 3-acyl-1,2,4-oxadiazoles [J].
Bottoni, A ;
Frenna, V ;
Lanza, CZ ;
Macaluso, G ;
Spinelli, D .
JOURNAL OF PHYSICAL CHEMISTRY A, 2004, 108 (10) :1731-1740
[9]  
Boulton A. J., 1973, LECT HETEROCYCLIC CH
[10]   HETEROCYCLIC REARRANGEMENTS .X. A GENERALISED MONOCYCLIC REARRANGEMENT [J].
BOULTON, AJ ;
KATRITZK.AR ;
HAMID, AM .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (20) :2005-&