An exploratory ab initio study on the conformations of ethylguanidine in its neutral [CH3-CH2-NH-C(=NH)NH2] and protonated [CH3-CH2-NH-C(NH2)2] forms

Melody L. Mak, Salvatore J. Salpietro, R. Daniel Enriz, I. Csizmadia

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

To explore the conformation intricacies of the guanidine group in the arginine side chain, ab initio computations have been carried out with ethylguanidine and the ethyl guanidinium ion. HF computations have been performed using 3-21G and 6-31G basis sets and DFT calculations were carried out at the B3LYP/6- 31G(d) level of theory. The ethyl guanidinium ion has a single isomer due to its internal symmetry, although this structure has at least three conformations. However, several structures were found and optimized for ethylguanidine, involving the endo- and exo- orientation of the lone NH and torsional angle χ6, as well as the torsional modes associated with χ4 and χ5 Torsional angle χ5 gives rise to s-cis and s-trans structures.

Original languageEnglish
Pages (from-to)626-641
Number of pages16
JournalCanadian Journal of Chemistry
Volume78
Issue number5
Publication statusPublished - 2000

Fingerprint

Guanidine
Conformations
Ions
Arginine
Discrete Fourier transforms
Isomers

Keywords

  • Ab initio MO
  • Arginine side-chain
  • Conformational analysis
  • Ethylguanidine
  • Ethylguanidinium ion

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

An exploratory ab initio study on the conformations of ethylguanidine in its neutral [CH3-CH2-NH-C(=NH)NH2] and protonated [CH3-CH2-NH-C(NH2)2] forms. / Mak, Melody L.; Salpietro, Salvatore J.; Enriz, R. Daniel; Csizmadia, I.

In: Canadian Journal of Chemistry, Vol. 78, No. 5, 2000, p. 626-641.

Research output: Contribution to journalArticle

@article{4cf97348da2144d495ab39eee772f2cb,
title = "An exploratory ab initio study on the conformations of ethylguanidine in its neutral [CH3-CH2-NH-C(=NH)NH2] and protonated [CH3-CH2-NH-C(NH2)2] forms",
abstract = "To explore the conformation intricacies of the guanidine group in the arginine side chain, ab initio computations have been carried out with ethylguanidine and the ethyl guanidinium ion. HF computations have been performed using 3-21G and 6-31G basis sets and DFT calculations were carried out at the B3LYP/6- 31G(d) level of theory. The ethyl guanidinium ion has a single isomer due to its internal symmetry, although this structure has at least three conformations. However, several structures were found and optimized for ethylguanidine, involving the endo- and exo- orientation of the lone NH and torsional angle χ6, as well as the torsional modes associated with χ4 and χ5 Torsional angle χ5 gives rise to s-cis and s-trans structures.",
keywords = "Ab initio MO, Arginine side-chain, Conformational analysis, Ethylguanidine, Ethylguanidinium ion",
author = "Mak, {Melody L.} and Salpietro, {Salvatore J.} and Enriz, {R. Daniel} and I. Csizmadia",
year = "2000",
language = "English",
volume = "78",
pages = "626--641",
journal = "Canadian Journal of Chemistry",
issn = "0008-4042",
publisher = "National Research Council of Canada",
number = "5",

}

TY - JOUR

T1 - An exploratory ab initio study on the conformations of ethylguanidine in its neutral [CH3-CH2-NH-C(=NH)NH2] and protonated [CH3-CH2-NH-C(NH2)2] forms

AU - Mak, Melody L.

AU - Salpietro, Salvatore J.

AU - Enriz, R. Daniel

AU - Csizmadia, I.

PY - 2000

Y1 - 2000

N2 - To explore the conformation intricacies of the guanidine group in the arginine side chain, ab initio computations have been carried out with ethylguanidine and the ethyl guanidinium ion. HF computations have been performed using 3-21G and 6-31G basis sets and DFT calculations were carried out at the B3LYP/6- 31G(d) level of theory. The ethyl guanidinium ion has a single isomer due to its internal symmetry, although this structure has at least three conformations. However, several structures were found and optimized for ethylguanidine, involving the endo- and exo- orientation of the lone NH and torsional angle χ6, as well as the torsional modes associated with χ4 and χ5 Torsional angle χ5 gives rise to s-cis and s-trans structures.

AB - To explore the conformation intricacies of the guanidine group in the arginine side chain, ab initio computations have been carried out with ethylguanidine and the ethyl guanidinium ion. HF computations have been performed using 3-21G and 6-31G basis sets and DFT calculations were carried out at the B3LYP/6- 31G(d) level of theory. The ethyl guanidinium ion has a single isomer due to its internal symmetry, although this structure has at least three conformations. However, several structures were found and optimized for ethylguanidine, involving the endo- and exo- orientation of the lone NH and torsional angle χ6, as well as the torsional modes associated with χ4 and χ5 Torsional angle χ5 gives rise to s-cis and s-trans structures.

KW - Ab initio MO

KW - Arginine side-chain

KW - Conformational analysis

KW - Ethylguanidine

KW - Ethylguanidinium ion

UR - http://www.scopus.com/inward/record.url?scp=0033934760&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0033934760&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0033934760

VL - 78

SP - 626

EP - 641

JO - Canadian Journal of Chemistry

JF - Canadian Journal of Chemistry

SN - 0008-4042

IS - 5

ER -