Quantum-chemical study of molecular structure and relative stability of trans and cis isomers of model anilide derivatives

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Abstract

Derivatives of anilide were studied systematically by the density functional theory (DFT) using the B3LYP hybrid functional and the 6-311+G(3df,2p) basis set. Characteristic frequencies of N-H and C=O stretching modes for cis and trans conformers distinguishing were compared with available experimental and theoretical data. Effect of substitution in ortho position and acidic residue group is discussed with respect to the bond length changes in the aromatic ring and aromaticity indexes. Energy differences between cis and trans conformations allow estimating the effect of intramolecular hydrogen bonds stabilizing the studied conformations. The trans conformation of parent formanilide is stabilized via the C(aromatic) -H∙∙∙O=C interaction with the energy of around 4 kJ・mol-1. The selected anilide series represent model compounds for drug design.

Becke AD (1988) Phys. Rev. A 38: 3098-3100.

Flukiger P, Luthi HP, Portmann S, Weber J (2000) MOLEKEL 4.3. Swiss Center for Scientific Computing: Manno, Switzerland, 2002.

Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA Jr., Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Keith T, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2013) Gaussian 09, Revision D.01, Gaussian, Inc. Wallingford CT.

Frizzo CP, Martins MA (2012) Struct. Chem. 23(2): 375-380.

Hansch C, Leo A, Taft RW (1991) Chem. Rev. 91(2): 165-195.

Ilieva S, Hadjieva B, Galabov B (1999) J. Mol. Struct. 508(1): 73-80.

Jug K, Koester AM (1990) J. Am. Chem. Soc. 112(19): 6772-6777.

Krygowski TM, Ste,pień BT (2005) Chem. Rev. 105(10): 3482-3512.

Lee C, Yang W, Parr RG (1988) Phys Rev B 37: 785-789.

Marochkin II, Dorofeeva OV (2013) Struct. Chem. 24(1): 233-242.

Moritz AG (1960) Spectrochim. Acta 16(10): 1176-1183.

Muller P (2009) Pure and Applied Chemistry 66(5): 1077-1184.

Raczyńska ED, Hallman M, Kolczyńska K, Stępniewski TM (2010) Symmetry 2(3): 1485-1509.

Siddall III TH, Stewart WE, Marston AL (1968) J. Phys. Chem. 72(6): 2135-2141.

SDBSWeb (2017) http://sdbs.db.aist.go.jp (National Institute of Advanced Industrial Science and Technology, date of access: 20. 9. 2017)

Taft RW (1953) J. Am. Chem. Soc. 75: 4538.

Acta Chimica Slovaca

The Journal of Slovak University of Technology in Bratislava

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