A structural study of fentanyl by DFT calculations, NMR and IR spectroscopy

被引：42

作者：

Asadi, Zahra ^{[1
]}

Esrafili, Mehdi D. ^{[2
]}

Vessally, Esmail ^{[3
]}

Asnaashariisfahani, Manzarbanou ^{[4
]}

Yahyaei, Saeideh ^{[5
]}

Khani, Ali ^{[5
]}

机构：

[1] Islamic Azad Univ, Miyaneh Branch, Young Researchers & Elite Club, Miyaneh, Iran

[2] Univ Maragheh, Dept Chem, Lab Theoret Chem, Maragheh, Iran

[3] Payame Noor Univ, Dept Chem, Tehran, Iran

[4] Islamic Azad Univ, North Tehran Branch, Dept Chem, Tehran, Iran

[5] Islamic Azad Univ, Miyaneh Branch, Dept Chem, Miyaneh, Iran

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2017年 / 1128卷

关键词：

Opiate agonists; DFT; Chemical shifts; M06; B3LYP; MEP; DENSITY FUNCTIONALS; AB-INITIO; SERIES;

D O I：

10.1016/j.molstruc.2016.09.027

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

N-(1-(2-phenethyl)-4-piperidinyl-N-phenyl-propanamide (fentanyl) is synthesized and characterized by FT-IR, H-1 NMR, C-13 NMR, mass spectroscopy and elemental analyses. The geometry optimization is performed using the B3LYP and M06 density functionals with 6-311 + G(d) and 6-311++G(d,p) basis sets. The complete assignments are performed on the basis of the potential energy distribution (PED) of the all vibrational modes. Almost a nice correlation is found between the calculated 13C chemical shifts and experimental data. The frontier molecular orbitals and molecular electrostatic potential of fentanyl are also obtained. (C) 2016 Elsevier B.V. All rights reserved.

引用

页码：552 / 562

页数：11

共 34 条

[1] Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures [J].

AbdelMagid, AF ;

Carson, KG ;

Harris, BD ;

Maryanoff, CA ;

Shah, RD .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3849-3862

[2] Quantitative analysis of molecular surfaces: areas, volumes, electrostatic potentials and average local ionization energies [J].

Bulat, Felipe A. ;

Toro-Labbe, Alejandro ;

Brinck, Tore ;

Murray, Jane S. ;

Politzer, Peter .

JOURNAL OF MOLECULAR MODELING, 2010, 16 (11) :1679-1691

[3]

Casy A.F., 1986, OPIOID ANALGESICS

[4]

Dennington R., 2007, Gaussview

[5] (1R)-2-[(3R,4S)-3-methyl-4-(N-phenyl-N-propionylamino)piperidin-1-yl]-1-phenylethyl p-bromobenzoate and N-{(3R,4S)-1-[(2S)-2-(4-bromo-phenyl)-2-hydroxyethyl]-3-methyl-piperidin-4-yl}-N-phenylacrylamide [J].

Deschamps, JR ;

George, C ;

Flippen-Anderson, JL .

ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 2002, 58 (06) :O362-O364

[6] An ab initio study on chalcogen-chalcogen bond interactions in cyclic (SHX)3 complexes (X = F, Cl, CN, NC, CCH, OH, OCH3, NH2) [J].

Esrafili, Mehdi D. ;

Mohammadian-Sabet, Fariba .

CHEMICAL PHYSICS LETTERS, 2015, 628 :71-75

[7] Nitrogen-doped (6,0) carbon nanotubes: A comparative DFT study based on surface reactivity descriptors [J].

Esrafili, Mehdi D. .

COMPUTATIONAL AND THEORETICAL CHEMISTRY, 2013, 1015 :1-7

[8]

Frisch M., 2004, GAUSSIAN 03 REVISION, DOI DOI 10.1016/J.MOLSTRUC.2017.03.014

[9] Gas chromatographic mass spectrometry and gas chromatographic Fourier transform infrared spectroscopy assay for the simultaneous identification of fentanyl metabolites [J].

Guitton, J ;

Desage, M ;

Alamercery, S ;

Dutruch, L ;

Dautraix, S ;

Perdrix, JP ;

Brazier, JL .

JOURNAL OF CHROMATOGRAPHY B, 1997, 693 (01) :59-70

[10] INVESTIGATIONS OF SUBSTITUENT EFFECTS BY NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY AND ALL-VALENCE ELECTRON MOLECULAR-ORBITAL CALCULATIONS .1. 4-SUBSTITUTED STYRENES [J].

HAMER, GK ;

PEAT, IR ;

REYNOLDS, WF .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1973, 51 (06) :897-914

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