Vibrational Spectroscopic Investigation and Conformational Analysis of Methacrylamidoantipyrine: A Comparative Density Functional Study

Özgür Alver,Metin Bilge,Cemal Parlak,Mehmet Fatih Kaya

doi:10.1155/2013/386247

Abstract

FT-IR and Raman spectra of methacrylamidoantipyrine (MAAP) have been reported in the region of 4000–10 cm−1 and 4000–100 cm−1, respectively. The optimized geometric parameters, conformational analysis, normal mode frequencies, and corresponding vibrational assignments of MAAP (C15H17N3O2) have been examined by means of density functional theory (DFT) method using the Becke-3-Lee-Yang-Parr (B3LYP) exchange-correlation functional and the 6-31G++(d,p) basis sets. Vibrational assignments have been made on the basis of potential energy distribution (PED) and the thermodynamics functions, and the highest occupied and the lowest unoccupied molecular orbitals (HOMO and LUMO) of MAAP have been predicted. Calculations are carried out with the possible seven (amide-1–5 and imide-1-2) conformational isomers of MAAP. Comparison between the experimental and theoretical results indicates that the B3LYP method provides satisfactory evidence for the prediction of vibrational wavenumbers, and the amide-1 conformational isomer is supposed to be the most stable form of MAAP.

Highlights

The MAAP, which has a π electron rich aromatic ring, was first synthesized using antipyrine, a hydroxy radical capture and spectroscopic reagent for phenols, and used for a method described for removal of phenolic compounds with nitrophenol imprinted polymer based on π-π and hydrogen bonding interactions [1]
We have reported vibrational spectra of MAAP
In order to show the relative contributions of the redundant internal coordinates to each normal vibrational mode of the molecule, potential energy distribution (PED) calculations were carried out by the vibrational energy distribution analysis 4 (VEDA) [18]

Summary

Introduction

The MAAP, which has a π electron rich aromatic ring, was first synthesized using antipyrine, a hydroxy radical capture and spectroscopic reagent for phenols, and used for a method described for removal of phenolic compounds with nitrophenol imprinted polymer based on π-π and hydrogen bonding interactions [1]. One can reach many papers published where it is one of the most important organic chemical product for the molecularly imprinted polymers [1,2,3,4,5] It has been used in researching the biomimetic immunoassay based on molecularly imprinted polymer [3], the 8-Hydroxy-2󸀠-deoxyguanosine (8-OHdG), which is one of the most abundant oxidative DNA lesions resulting from reactive oxygen species, and the 8-OHdG level in blood serum from a breast cancer patient [4], and new 8-OHdG imprinted quartz crystal microbalance sensor [5]. The results of the theoretical and spectroscopic studies are reported here

Experimental

Calculations

Results and Discussion

Conclusion