Quantum study on the electrocyclic reactions of CH2CHCHCHX (X==H, F, Cl)

Ping Deng; L. I. Lai-Cai; A.N.-Min Tian; Ning-Bew Wong

doi:10.1002/qua.20159

Quantum study on the electrocyclic reactions of CH₂CHCHCHX (X==H, F, Cl)

Ping Deng
, L. I. Lai-Cai
, A.N.-Min Tian
, Ning-Bew Wong

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

2 Citations (Scopus)

Abstract

The microscopic mechanisms of the electrocyclic reactions for cis-1,3-butadiene and its monofluoro-, monochloroderivatives have been studied by density functional theory (DFT), using the B3LYP method and 6-311++G** basis sets. We optimized the geometric configurations of reactants, transition states, and products; verified all the probable transition states through vibrational analysis; and calculated the relative single-point energies at the QCISD(T)/6-311++G**//B3LYP/6-311++G**. The results show that the monofluoro-, monochloroderivatives of cis-1,3-butadiene both have two conformers; the reactant favors the electrocyclic reaction when one outboard hydrogen atom of the CH₂ groups is substituted by the fluorine or chlorine atom. © 2004 Wiley Periodicals, Inc.

Original language	English
Pages (from-to)	288-292
Journal	International Journal of Quantum Chemistry
Volume	100
Issue number	3
DOIs	https://doi.org/10.1002/qua.20159
Publication status	Published - 5 Nov 2004

Bibliographical note

Publication details (e.g. title, author(s), publication statuses and dates) are captured on an “AS IS” and “AS AVAILABLE” basis at the time of record harvesting from the data source. Suggestions for further amendments or supplementary information can be sent to [email protected].

Research Keywords

3-butadiene
Cis-1
Density functional theory
Monohalogen-butadiene
Transition states

Access Output

10.1002/qua.20159

Other Access Options

Check CityUHK Library

Permanent Link

Right click to copy link

Cite this

@article{62562fd328c041c790d113de20038343,

title = "Quantum study on the electrocyclic reactions of CH2CHCHCHX (X==H, F, Cl)",

abstract = "The microscopic mechanisms of the electrocyclic reactions for cis-1,3-butadiene and its monofluoro-, monochloroderivatives have been studied by density functional theory (DFT), using the B3LYP method and 6-311++G** basis sets. We optimized the geometric configurations of reactants, transition states, and products; verified all the probable transition states through vibrational analysis; and calculated the relative single-point energies at the QCISD(T)/6-311++G**//B3LYP/6-311++G**. The results show that the monofluoro-, monochloroderivatives of cis-1,3-butadiene both have two conformers; the reactant favors the electrocyclic reaction when one outboard hydrogen atom of the CH2 groups is substituted by the fluorine or chlorine atom. {\textcopyright} 2004 Wiley Periodicals, Inc.",

keywords = "3-butadiene, Cis-1, Density functional theory, Monohalogen-butadiene, Transition states",

author = "Ping Deng and Lai-Cai, \{L. I.\} and A.N.-Min Tian and Ning-Bew Wong",

note = "Publication details (e.g. title, author(s), publication statuses and dates) are captured on an “AS IS” and “AS AVAILABLE” basis at the time of record harvesting from the data source. Suggestions for further amendments or supplementary information can be sent to [email protected].",

year = "2004",

month = nov,

day = "5",

doi = "10.1002/qua.20159",

language = "English",

volume = "100",

pages = "288--292",

journal = "International Journal of Quantum Chemistry",

issn = "0020-7608",

publisher = "John Wiley \& Sons",

number = "3",

}

TY - JOUR

T1 - Quantum study on the electrocyclic reactions of CH2CHCHCHX (X==H, F, Cl)

AU - Deng, Ping

AU - Lai-Cai, L. I.

AU - Tian, A.N.-Min

AU - Wong, Ning-Bew

N1 - Publication details (e.g. title, author(s), publication statuses and dates) are captured on an “AS IS” and “AS AVAILABLE” basis at the time of record harvesting from the data source. Suggestions for further amendments or supplementary information can be sent to [email protected].

PY - 2004/11/5

Y1 - 2004/11/5

N2 - The microscopic mechanisms of the electrocyclic reactions for cis-1,3-butadiene and its monofluoro-, monochloroderivatives have been studied by density functional theory (DFT), using the B3LYP method and 6-311++G** basis sets. We optimized the geometric configurations of reactants, transition states, and products; verified all the probable transition states through vibrational analysis; and calculated the relative single-point energies at the QCISD(T)/6-311++G**//B3LYP/6-311++G**. The results show that the monofluoro-, monochloroderivatives of cis-1,3-butadiene both have two conformers; the reactant favors the electrocyclic reaction when one outboard hydrogen atom of the CH2 groups is substituted by the fluorine or chlorine atom. © 2004 Wiley Periodicals, Inc.

AB - The microscopic mechanisms of the electrocyclic reactions for cis-1,3-butadiene and its monofluoro-, monochloroderivatives have been studied by density functional theory (DFT), using the B3LYP method and 6-311++G** basis sets. We optimized the geometric configurations of reactants, transition states, and products; verified all the probable transition states through vibrational analysis; and calculated the relative single-point energies at the QCISD(T)/6-311++G**//B3LYP/6-311++G**. The results show that the monofluoro-, monochloroderivatives of cis-1,3-butadiene both have two conformers; the reactant favors the electrocyclic reaction when one outboard hydrogen atom of the CH2 groups is substituted by the fluorine or chlorine atom. © 2004 Wiley Periodicals, Inc.

KW - 3-butadiene

KW - Cis-1

KW - Density functional theory

KW - Monohalogen-butadiene

KW - Transition states

UR - https://www.scopus.com/pages/publications/6344280614

UR - https://www.scopus.com/record/pubmetrics.uri?eid=2-s2.0-6344280614&origin=recordpage

U2 - 10.1002/qua.20159

DO - 10.1002/qua.20159

M3 - RGC 21 - Publication in refereed journal

SN - 0020-7608

VL - 100

SP - 288

EP - 292

JO - International Journal of Quantum Chemistry

JF - International Journal of Quantum Chemistry

IS - 3

ER -