DFT and MP2 study of the molecular structure and vibrational spectra of the anticancer agent cyclophosphamide

Hassan M. Badawi; Wolfgang Förner

doi:10.5560/ZNB.2012-0069

DFT and MP2 study of the molecular structure and vibrational spectra of the anticancer agent cyclophosphamide

Hassan M. Badawi
, Wolfgang Förner^*

^*Corresponding author for this work

King Fahd University of Petroleum & Minerals

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

Abstract

The possible conformations in the most stable structure of cyclophosphamide were investigated at the DFT-B3LYP and MP2/6-311G**levels of calculation. The axial structure is calculated to be lower in energy than the equatorial form of cyclophosphamide by 5 (MP2) to 6 (DFT) kcal mol^-1 because of a very weak anomeric effect and weak conjugation. Further it is the same structure as the one found in the X-ray investigations both of the hydrate and of the anhydrous form. The computed DFT vibrational frequencies of the axial structure were used to analyze the infrared and Raman spectra using normal-coordinate calculations to provide reliable assignments to the normal modes of the molecule.

Original language	English
Pages (from-to)	1305-1313
Number of pages	9
Journal	Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences
Volume	67
Issue number	12
DOIs	https://doi.org/10.5560/ZNB.2012-0069
State	Published - Dec 2012

Bibliographical note

Funding Information:
The authors gratefully acknowledge the support of this work by King Fahd University of Petroleum and Minerals.

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

Anticancer Agent
Conformational Structure
Cyclophosphamide
N
N-Bis(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amine-2-oxide
Vibrational Spectra

ASJC Scopus subject areas

General Chemistry

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10.5560/ZNB.2012-0069

Cite this

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title = "DFT and MP2 study of the molecular structure and vibrational spectra of the anticancer agent cyclophosphamide",

abstract = "The possible conformations in the most stable structure of cyclophosphamide were investigated at the DFT-B3LYP and MP2/6-311G**levels of calculation. The axial structure is calculated to be lower in energy than the equatorial form of cyclophosphamide by 5 (MP2) to 6 (DFT) kcal mol-1 because of a very weak anomeric effect and weak conjugation. Further it is the same structure as the one found in the X-ray investigations both of the hydrate and of the anhydrous form. The computed DFT vibrational frequencies of the axial structure were used to analyze the infrared and Raman spectra using normal-coordinate calculations to provide reliable assignments to the normal modes of the molecule.",

keywords = "Anticancer Agent, Conformational Structure, Cyclophosphamide, N, N-Bis(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amine-2-oxide, Vibrational Spectra",

author = "Badawi, \{Hassan M.\} and Wolfgang F{\"o}rner",

note = "Funding Information: The authors gratefully acknowledge the support of this work by King Fahd University of Petroleum and Minerals.",

year = "2012",

month = dec,

doi = "10.5560/ZNB.2012-0069",

language = "English",

volume = "67",

pages = "1305--1313",

journal = "Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences",

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publisher = "Walter de Gruyter GmbH",

number = "12",

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TY - JOUR

T1 - DFT and MP2 study of the molecular structure and vibrational spectra of the anticancer agent cyclophosphamide

AU - Badawi, Hassan M.

AU - Förner, Wolfgang

N1 - Funding Information: The authors gratefully acknowledge the support of this work by King Fahd University of Petroleum and Minerals.

PY - 2012/12

Y1 - 2012/12

N2 - The possible conformations in the most stable structure of cyclophosphamide were investigated at the DFT-B3LYP and MP2/6-311G**levels of calculation. The axial structure is calculated to be lower in energy than the equatorial form of cyclophosphamide by 5 (MP2) to 6 (DFT) kcal mol-1 because of a very weak anomeric effect and weak conjugation. Further it is the same structure as the one found in the X-ray investigations both of the hydrate and of the anhydrous form. The computed DFT vibrational frequencies of the axial structure were used to analyze the infrared and Raman spectra using normal-coordinate calculations to provide reliable assignments to the normal modes of the molecule.

AB - The possible conformations in the most stable structure of cyclophosphamide were investigated at the DFT-B3LYP and MP2/6-311G**levels of calculation. The axial structure is calculated to be lower in energy than the equatorial form of cyclophosphamide by 5 (MP2) to 6 (DFT) kcal mol-1 because of a very weak anomeric effect and weak conjugation. Further it is the same structure as the one found in the X-ray investigations both of the hydrate and of the anhydrous form. The computed DFT vibrational frequencies of the axial structure were used to analyze the infrared and Raman spectra using normal-coordinate calculations to provide reliable assignments to the normal modes of the molecule.

KW - Anticancer Agent

KW - Conformational Structure

KW - Cyclophosphamide

KW - N

KW - N-Bis(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amine-2-oxide

KW - Vibrational Spectra

UR - https://www.scopus.com/pages/publications/84872123365

U2 - 10.5560/ZNB.2012-0069

DO - 10.5560/ZNB.2012-0069

M3 - Article

AN - SCOPUS:84872123365

SN - 0932-0776

VL - 67

SP - 1305

EP - 1313

JO - Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

JF - Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

IS - 12

ER -

DFT and MP2 study of the molecular structure and vibrational spectra of the anticancer agent cyclophosphamide

Abstract

Bibliographical note

UN SDGs

Keywords

ASJC Scopus subject areas

Access to Document

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Cite this