DFT versus Moller-Plesset conformational profile and vibrational assignments of non-planar phenoxyacetic acid and 2,3,4,5,6-pentafluorophenoxyacetic acid

被引:9
作者
Badawi, Hassan M. [1 ]
机构
[1] King Fahd Univ Petr & Minerals, Dept Chem, Dhahran 31261, Saudi Arabia
关键词
Structural stability; Vibrational spectra and assignments; Phenoxyacetic acid; 2,3,4,5,6-Pentafluorophenoxyacetic acid; DERIVATIVES; HERBICIDES;
D O I
10.1016/j.molstruc.2010.05.012
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The structural stability of phenoxyacetic acid and 2,3,4,5,6-pentafluorphenoxyacetic acid was investigated by the DFT-B3LYP and the ab initio MP2 calculations with the 6-311G** basis set. For the parent acid the calculations were extended to the MP4(SDQ) level of theory. At the DFT-B3LYP level of calculation the planar Tttp (transoid O=C-O-H) was predicted to be about 0.5 and 1.3 kcal/mol lower in energy than the non-planar Cgcpp and Tgcpp (cisoid O=C-O-H) forms, respectively. At the MP2 and the MP4(SDQ) levels the Cgcpp form was predicted to be about 0.8 and 1.4 kcal/mol lower in energy than the Tgcpp and the Tttcp structures, respectively. On the basis of the Moller-Plesset calculations the Cgcpp and the Tgcpp conformations were adopted as the low and high energy structures of phenoxyacetic acid. The observed spectral intensities of phenoxyacetic acid were consistence with the Cgcpp conformation being the predominant form of the acid at room temperature. At the DFT and MP2 levels of theory 2,3,4,5,6-pentafluorophenoxyacetic acid was predicted to exist predominantly in the Cgcpp structure. The vibrational wavenumbers were computed at the B3LYP level of theory and tentative vibrational assignments were provided on the basis of combined theoretical and experimental infrared and Raman data of both molecules. (C) 2010 Elsevier B.V. All rights reserved.
引用
收藏
页码:67 / 71
页数:5
相关论文
共 13 条
[1]   Discovery of novel phenoxyacetic acid derivatives as antimycobacterial agents [J].
Ali, Mohamed Ashraf ;
Shaharyar, Mohammad .
BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (05) :1896-1902
[2]   Structural stability, NH2 inversion and vibrational assignments of 2,4,6-trichloroaniline and 2,3,5,6-tetrachloroaniline [J].
Badawi, Hassan M. ;
Foerner, Wolfgang ;
Al-Saadi, Abdulaziz A. .
JOURNAL OF MOLECULAR STRUCTURE, 2009, 938 (1-3) :41-47
[3]  
Dennington R., 2008, GaussView Version 5.0.8
[4]   Erythrocyte membrane protein damage by phenoxyacetic herbicides and their metabolites [J].
Duchnowicz, P ;
Szczepaniak, P ;
Koter, M .
PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY, 2005, 82 (01) :59-65
[5]  
Frisch M., 2004, GAUSSIAN 03 REVISION, DOI DOI 10.1016/J.MOLSTRUC.2017.03.014
[6]   Allergic reaction induced by dermal and/or respiratory exposure to low-dose phenoxyacetic acid, organophosphorus, and carbamate pesticides [J].
Fukuyama, Tomoki ;
Tajima, Yukari ;
Ueda, Hideo ;
Hayashi, Koichi ;
Shutoh, Yasufumi ;
Harada, Takanori ;
Kosaka, Tadashi .
TOXICOLOGY, 2009, 261 (03) :152-161
[7]   Raman spectral analysis of phenoxyacetic acid and some chloro substituted phenoxyacetic acids [J].
Karthikeyan, B ;
Saravanan, B .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2006, 63 (03) :619-623
[8]   Uptake of phenoxyacetic acid derivatives into Caco-2 cells by the monocarboxylic acid transporters [J].
Kimura, Osamu ;
Tsukagoshi, Kensuke ;
Endo, Tetsuya .
TOXICOLOGY LETTERS, 2009, 189 (02) :102-109
[9]   UNIVALENT METAL-COMPLEXES OF (PERFLUOROPHENOXY)ACETIC ACID - THE CRYSTAL-STRUCTURES OF (2,3,4,5,6-PENTAFLUOROPHENOXY)ACETIC ACID, BIS-MU-[(2,3,4,5,6-PENTAFLUOROPHENOXY)ACETATO-O,O']-BISSILVER(I) AND CATENA-BIS-MU-[(2,3,4,5,6-PENTAFLUOROPHENOXY)ACETATO-O]-BISMERCURY(I [J].
MAK, TCW ;
YIP, WH ;
KENNARD, CHL ;
SMITH, G ;
OREILLY, EJ .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1988, 41 (05) :683-691
[10]  
SDBSWeb, SDBSWEB