ICCAS OpenIR
The conformation of N-phenylmethylene-2-thiazoleamine species and the driving forces for twisting molecule
Yu, ZH; Xuan, ZQ; Guo, YS; Peng, XQ; Wang, TX; Jin, XL
2001
Source PublicationCHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE
ISSN0251-0790
Volume22Issue:1Pages:122-126
AbstractThe crystal structures of N-phenylmethylene-2-thiazoleamine (2a) and N-[(4-nitrophenyl) methylene]-2-thiazoleamine (2b) were determined. Twenty-two rotational geometries(theta =0 degrees similar to 90 degrees) of each of two molecules were optimized using AM1, RHF/6-311G**, B3LYP/6-311G and B3LYP/6-311G**. The twist angles of their preferential geometries obtained from DFT are both 0 degrees, which are most close to the experimental values (2a, theta =8, 9 degrees; 2b, theta =3, 9 degrees) of all angles obtained from various optimized methods. Although there is a great difference in the twist angles of the five molecules, 2a, 2b, N-(4-nitrophrnyl)methylene-2-pyrimidineamine (la), N-(4-nitrophenyl) methylene-2-pyridine-amine (Ib) and N-phenyl) methylene-3-pyridineamine (Ic), their lowest total electronic energies occur in the optimized geometries with the similar twist angles which are in the region of theta from 37 to 42 degrees and almost have nothing to do with the optimized methods (HF and DFT) and Gaussian basis sets. The pi system in the geometry with theta =0 degrees is destabilized no matter whether it is delocalized or not. It appears that the pi system always prefers a twisted geometry. The driving force for out-of-plane twist of the molecules arises from the electronic interaction, and the nuclear repulsion is, practically, a resistance for distortion of molecule.
KeywordResonance Effect Driving Force For Distorting Stilbene-like Species Conformation N-phenylmethylene-2-thiazoleameine N-(4-nitrophemyl)Methylene-2-thiazoleameine
Indexed BySCI
Language英语
WOS IDWOS:000167569400032
PublisherHIGHER EDUCATION PRESS
Citation statistics
Cited Times:5[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/77530
Collection中国科学院化学研究所
Corresponding AuthorYu, ZH
Affiliation1.Chinese Acad Sci, Inst Chem, State Key Lab Stable & Unstable Species, Beijing 100080, Peoples R China
2.Peking Univ, Inst Chem & Mol Engn, State Key Lab Stable & Unstable Species, Beijing 100871, Peoples R China
Recommended Citation
GB/T 7714
Yu, ZH,Xuan, ZQ,Guo, YS,et al. The conformation of N-phenylmethylene-2-thiazoleamine species and the driving forces for twisting molecule[J]. CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE,2001,22(1):122-126.
APA Yu, ZH,Xuan, ZQ,Guo, YS,Peng, XQ,Wang, TX,&Jin, XL.(2001).The conformation of N-phenylmethylene-2-thiazoleamine species and the driving forces for twisting molecule.CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE,22(1),122-126.
MLA Yu, ZH,et al."The conformation of N-phenylmethylene-2-thiazoleamine species and the driving forces for twisting molecule".CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE 22.1(2001):122-126.
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