Theoretical investigations on the molecular structure, vibrational spectra, HOMO-LUMO analyses and NBO study of 1-[(Cyclopropylmethoxy)methyl]-5-ethyl-6- (4-methylbenzyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione

Ebtehal S. Al-Abdullah; Y. Sheena Mary; C. Yohannan Panicker; Nasser R. El-Brollosy; Ali A. El-Emam; Christian Van Alsenoy; Abdulaziz A. Al-Saadi

doi:10.1016/j.saa.2014.06.042

Theoretical investigations on the molecular structure, vibrational spectra, HOMO-LUMO analyses and NBO study of 1-[(Cyclopropylmethoxy)methyl]-5-ethyl-6- (4-methylbenzyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione

Ebtehal S. Al-Abdullah
, Y. Sheena Mary
, C. Yohannan Panicker^*
, Nasser R. El-Brollosy
, Ali A. El-Emam
, Christian Van Alsenoy
, Abdulaziz A. Al-Saadi

^*Corresponding author for this work

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

32 Scopus citations

Abstract

The FT-IR and FT-Raman spectra of 1-[(Cyclopropylmethoxy)methyl]-5-ethyl-6- (4-methylbenzyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione were recorded. In this work, experimental and theoretical study on the molecular structure and vibrational wavenumbers of the title compound are presented. The vibrational wavenumbers were obtained theoretically at the DFT level and were compared with the experimental results. The study is extended to calculate the HOMO-LUMO energy gap, NBO, mapped molecular electrostatic potential and first hyperpolarizability. The calculated first hyperpolarizability of the title compound is 9.15 times that of urea and hence the title compound and the series of compounds it represents are attractive candidates for further studies in non linear optical applications. In the title compound, the HOMO of π nature is delocalized over the phenyl ring while the LUMO is located over the pyrimidine ring. The inter-molecular hydrogen bonding at O₇ and N ₁H₂₅ positions in each monomer give rise to a C ₂-symmetry dimer which is predicted to be about 10 kcal mol ^-1 more stable than the monomeric form.

Original language	English
Pages (from-to)	639-650
Number of pages	12
Journal	Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
Volume	133
DOIs	https://doi.org/10.1016/j.saa.2014.06.042
State	Published - 10 Dec 2014

Bibliographical note

Funding Information:
The authors would like to extend their sincere appreciation to the Deanship of Scientific Research at Kings Saud University , Saudi Arabia for funding this work through the Research Group Project No. RGP-362 . The authors are thankful to University of Antwerp for access to the University’s CalcUA Supercomputer Cluster.

Keywords

Cyclopropyl
FT-Raman
FTIR
Methoxy
Pyrimidine

ASJC Scopus subject areas

Analytical Chemistry
Atomic and Molecular Physics, and Optics
Instrumentation
Spectroscopy

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Al-Abdullah, E. S., Mary, Y. S., Panicker, C. Y., El-Brollosy, N. R., El-Emam, A. A., Van Alsenoy, C., & Al-Saadi, A. A. (2014). Theoretical investigations on the molecular structure, vibrational spectra, HOMO-LUMO analyses and NBO study of 1-[(Cyclopropylmethoxy)methyl]-5-ethyl-6- (4-methylbenzyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione. Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 133, 639-650. https://doi.org/10.1016/j.saa.2014.06.042

Al-Abdullah, Ebtehal S. ; Mary, Y. Sheena ; Panicker, C. Yohannan et al. / Theoretical investigations on the molecular structure, vibrational spectra, HOMO-LUMO analyses and NBO study of 1-[(Cyclopropylmethoxy)methyl]-5-ethyl-6- (4-methylbenzyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione. In: Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy. 2014 ; Vol. 133. pp. 639-650.

@article{7ad00370a44a44e48b456454151f2dd1,

title = "Theoretical investigations on the molecular structure, vibrational spectra, HOMO-LUMO analyses and NBO study of 1-[(Cyclopropylmethoxy)methyl]-5-ethyl-6- (4-methylbenzyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione",

abstract = "The FT-IR and FT-Raman spectra of 1-[(Cyclopropylmethoxy)methyl]-5-ethyl-6- (4-methylbenzyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione were recorded. In this work, experimental and theoretical study on the molecular structure and vibrational wavenumbers of the title compound are presented. The vibrational wavenumbers were obtained theoretically at the DFT level and were compared with the experimental results. The study is extended to calculate the HOMO-LUMO energy gap, NBO, mapped molecular electrostatic potential and first hyperpolarizability. The calculated first hyperpolarizability of the title compound is 9.15 times that of urea and hence the title compound and the series of compounds it represents are attractive candidates for further studies in non linear optical applications. In the title compound, the HOMO of π nature is delocalized over the phenyl ring while the LUMO is located over the pyrimidine ring. The inter-molecular hydrogen bonding at O7 and N 1H25 positions in each monomer give rise to a C 2-symmetry dimer which is predicted to be about 10 kcal mol -1 more stable than the monomeric form.",

keywords = "Cyclopropyl, FT-Raman, FTIR, Methoxy, Pyrimidine",

author = "Al-Abdullah, \{Ebtehal S.\} and Mary, \{Y. Sheena\} and Panicker, \{C. Yohannan\} and El-Brollosy, \{Nasser R.\} and El-Emam, \{Ali A.\} and \{Van Alsenoy\}, Christian and Al-Saadi, \{Abdulaziz A.\}",

note = "Funding Information: The authors would like to extend their sincere appreciation to the Deanship of Scientific Research at Kings Saud University , Saudi Arabia for funding this work through the Research Group Project No. RGP-362 . The authors are thankful to University of Antwerp for access to the University{\textquoteright}s CalcUA Supercomputer Cluster. ",

year = "2014",

month = dec,

day = "10",

doi = "10.1016/j.saa.2014.06.042",

language = "English",

volume = "133",

pages = "639--650",

journal = "Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy",

issn = "1386-1425",

publisher = "Elsevier B.V.",

}

Al-Abdullah, ES, Mary, YS, Panicker, CY, El-Brollosy, NR, El-Emam, AA, Van Alsenoy, C & Al-Saadi, AA 2014, 'Theoretical investigations on the molecular structure, vibrational spectra, HOMO-LUMO analyses and NBO study of 1-[(Cyclopropylmethoxy)methyl]-5-ethyl-6- (4-methylbenzyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione', Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, vol. 133, pp. 639-650. https://doi.org/10.1016/j.saa.2014.06.042

Theoretical investigations on the molecular structure, vibrational spectra, HOMO-LUMO analyses and NBO study of 1-[(Cyclopropylmethoxy)methyl]-5-ethyl-6- (4-methylbenzyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione. / Al-Abdullah, Ebtehal S.; Mary, Y. Sheena; Panicker, C. Yohannan et al.
In: Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, Vol. 133, 10.12.2014, p. 639-650.

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

TY - JOUR

T1 - Theoretical investigations on the molecular structure, vibrational spectra, HOMO-LUMO analyses and NBO study of 1-[(Cyclopropylmethoxy)methyl]-5-ethyl-6- (4-methylbenzyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione

AU - Al-Abdullah, Ebtehal S.

AU - Mary, Y. Sheena

AU - Panicker, C. Yohannan

AU - El-Brollosy, Nasser R.

AU - El-Emam, Ali A.

AU - Van Alsenoy, Christian

AU - Al-Saadi, Abdulaziz A.

N1 - Funding Information: The authors would like to extend their sincere appreciation to the Deanship of Scientific Research at Kings Saud University , Saudi Arabia for funding this work through the Research Group Project No. RGP-362 . The authors are thankful to University of Antwerp for access to the University’s CalcUA Supercomputer Cluster.

PY - 2014/12/10

Y1 - 2014/12/10

N2 - The FT-IR and FT-Raman spectra of 1-[(Cyclopropylmethoxy)methyl]-5-ethyl-6- (4-methylbenzyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione were recorded. In this work, experimental and theoretical study on the molecular structure and vibrational wavenumbers of the title compound are presented. The vibrational wavenumbers were obtained theoretically at the DFT level and were compared with the experimental results. The study is extended to calculate the HOMO-LUMO energy gap, NBO, mapped molecular electrostatic potential and first hyperpolarizability. The calculated first hyperpolarizability of the title compound is 9.15 times that of urea and hence the title compound and the series of compounds it represents are attractive candidates for further studies in non linear optical applications. In the title compound, the HOMO of π nature is delocalized over the phenyl ring while the LUMO is located over the pyrimidine ring. The inter-molecular hydrogen bonding at O7 and N 1H25 positions in each monomer give rise to a C 2-symmetry dimer which is predicted to be about 10 kcal mol -1 more stable than the monomeric form.

AB - The FT-IR and FT-Raman spectra of 1-[(Cyclopropylmethoxy)methyl]-5-ethyl-6- (4-methylbenzyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione were recorded. In this work, experimental and theoretical study on the molecular structure and vibrational wavenumbers of the title compound are presented. The vibrational wavenumbers were obtained theoretically at the DFT level and were compared with the experimental results. The study is extended to calculate the HOMO-LUMO energy gap, NBO, mapped molecular electrostatic potential and first hyperpolarizability. The calculated first hyperpolarizability of the title compound is 9.15 times that of urea and hence the title compound and the series of compounds it represents are attractive candidates for further studies in non linear optical applications. In the title compound, the HOMO of π nature is delocalized over the phenyl ring while the LUMO is located over the pyrimidine ring. The inter-molecular hydrogen bonding at O7 and N 1H25 positions in each monomer give rise to a C 2-symmetry dimer which is predicted to be about 10 kcal mol -1 more stable than the monomeric form.

KW - Cyclopropyl

KW - FT-Raman

KW - FTIR

KW - Methoxy

KW - Pyrimidine

UR - https://www.scopus.com/pages/publications/84903740804

U2 - 10.1016/j.saa.2014.06.042

DO - 10.1016/j.saa.2014.06.042

M3 - Article

C2 - 24992922

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SN - 1386-1425

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EP - 650

JO - Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

JF - Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

ER -

Al-Abdullah ES, Mary YS, Panicker CY, El-Brollosy NR, El-Emam AA, Van Alsenoy C et al. Theoretical investigations on the molecular structure, vibrational spectra, HOMO-LUMO analyses and NBO study of 1-[(Cyclopropylmethoxy)methyl]-5-ethyl-6- (4-methylbenzyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione. Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy. 2014 Dec 10;133:639-650. doi: 10.1016/j.saa.2014.06.042