The molecular structure and vibrational, 1H and 13C NMR spectra of lidocaine hydrochloride monohydrate

Hassan M. Badawi; Wolfgang Förner; Shaikh A. Ali

doi:10.1016/j.saa.2015.07.060

The molecular structure and vibrational, ¹H and ¹³C NMR spectra of lidocaine hydrochloride monohydrate

Hassan M. Badawi^*
, Wolfgang Förner
, Shaikh A. Ali

^*Corresponding author for this work

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

19 Scopus citations

Abstract

The structure, vibrational and NMR spectra of the local anesthetic drug lidocaine hydrochloride monohydrate salt were investigated by B3LYP/6-311G∗∗ calculations. The lidocaine·HCl·H₂O salt is predicted to have the gauche structure as the predominant form at ambient temperature with NCCN and CNCC torsional angles of 110° and -123° as compared to 10° and -64°, respectively in the base lidocaine. The repulsive interaction between the two N-H bonds destabilized the gauche structure of lidocaine·HCl·H₂O salt. The analysis of the observed vibrational spectra is consistent with the presence of the lidocaine salt in only one gauche conformation at room temperature. The ¹H and ¹³C NMR spectra of lidocaine·HCl·H₂O were interpreted by experimental and DFT calculated chemical shifts of the lidocaine salt. The RMSD between experimental and theoretical ¹H and ¹³C chemical shifts for lidocaine·HCl·H₂O is 2.32 and 8.21 ppm, respectively.

Original language	English
Pages (from-to)	92-100
Number of pages	9
Journal	Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
Volume	152
DOIs	https://doi.org/10.1016/j.saa.2015.07.060
State	Published - 20 Jul 2016

Bibliographical note

Publisher Copyright:
© 2015 Elsevier B.V. All rights reserved.

Keywords

Lidocaine hydrochloride monohydrate
Local anesthetic drug
Molecular structure
Vibrational H and C NMR spectra and assignments

ASJC Scopus subject areas

Analytical Chemistry
Atomic and Molecular Physics, and Optics
Instrumentation
Spectroscopy

Access to Document

10.1016/j.saa.2015.07.060

Cite this

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title = "The molecular structure and vibrational, 1H and 13C NMR spectra of lidocaine hydrochloride monohydrate",

abstract = "The structure, vibrational and NMR spectra of the local anesthetic drug lidocaine hydrochloride monohydrate salt were investigated by B3LYP/6-311G∗∗ calculations. The lidocaine·HCl·H2O salt is predicted to have the gauche structure as the predominant form at ambient temperature with NCCN and CNCC torsional angles of 110° and -123° as compared to 10° and -64°, respectively in the base lidocaine. The repulsive interaction between the two N-H bonds destabilized the gauche structure of lidocaine·HCl·H2O salt. The analysis of the observed vibrational spectra is consistent with the presence of the lidocaine salt in only one gauche conformation at room temperature. The 1H and 13C NMR spectra of lidocaine·HCl·H2O were interpreted by experimental and DFT calculated chemical shifts of the lidocaine salt. The RMSD between experimental and theoretical 1H and 13C chemical shifts for lidocaine·HCl·H2O is 2.32 and 8.21 ppm, respectively.",

keywords = "Lidocaine hydrochloride monohydrate, Local anesthetic drug, Molecular structure, Vibrational H and C NMR spectra and assignments",

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

year = "2016",

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doi = "10.1016/j.saa.2015.07.060",

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T1 - The molecular structure and vibrational, 1H and 13C NMR spectra of lidocaine hydrochloride monohydrate

AU - Badawi, Hassan M.

AU - Förner, Wolfgang

AU - Ali, Shaikh A.

PY - 2016/7/20

Y1 - 2016/7/20

N2 - The structure, vibrational and NMR spectra of the local anesthetic drug lidocaine hydrochloride monohydrate salt were investigated by B3LYP/6-311G∗∗ calculations. The lidocaine·HCl·H2O salt is predicted to have the gauche structure as the predominant form at ambient temperature with NCCN and CNCC torsional angles of 110° and -123° as compared to 10° and -64°, respectively in the base lidocaine. The repulsive interaction between the two N-H bonds destabilized the gauche structure of lidocaine·HCl·H2O salt. The analysis of the observed vibrational spectra is consistent with the presence of the lidocaine salt in only one gauche conformation at room temperature. The 1H and 13C NMR spectra of lidocaine·HCl·H2O were interpreted by experimental and DFT calculated chemical shifts of the lidocaine salt. The RMSD between experimental and theoretical 1H and 13C chemical shifts for lidocaine·HCl·H2O is 2.32 and 8.21 ppm, respectively.

AB - The structure, vibrational and NMR spectra of the local anesthetic drug lidocaine hydrochloride monohydrate salt were investigated by B3LYP/6-311G∗∗ calculations. The lidocaine·HCl·H2O salt is predicted to have the gauche structure as the predominant form at ambient temperature with NCCN and CNCC torsional angles of 110° and -123° as compared to 10° and -64°, respectively in the base lidocaine. The repulsive interaction between the two N-H bonds destabilized the gauche structure of lidocaine·HCl·H2O salt. The analysis of the observed vibrational spectra is consistent with the presence of the lidocaine salt in only one gauche conformation at room temperature. The 1H and 13C NMR spectra of lidocaine·HCl·H2O were interpreted by experimental and DFT calculated chemical shifts of the lidocaine salt. The RMSD between experimental and theoretical 1H and 13C chemical shifts for lidocaine·HCl·H2O is 2.32 and 8.21 ppm, respectively.

KW - Lidocaine hydrochloride monohydrate

KW - Local anesthetic drug

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KW - Vibrational H and C NMR spectra and assignments

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