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

• The structure of lidocaine·HCl·H2O was optimized at the DFT B3LYP level.
• The vibrational wavenumbers and NMR chemical shifts were calculated.
• Vibrational and NMR assignments were provided by combining experimental and theoretical data.

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.

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