Structural, electronic, topological and vibrational properties of a series of N-benzyl amides derived from Maca (Lepidium meyenii) combining spectroscopic studies with ONION calculations

CHAIN, FERNANDO EZEQUIEL; CATALÁN, CESAR ATILIO NAZARENO; GRAU, ALFREDO; MARIA FLORENCIA LADETTO; BRANDÁN, SILVIA ANTONIA

JOURNAL OF MOLECULAR STRUCTURE

ELSEVIER SCIENCE BV

Lugar: Amsterdam; Año: 2016 vol. 1105 p. 403 - 414

0022-2860

In the present work, the structural, topological and vibrational properties of four members of the Nbenzylamidesseries derived from Maca (Lepidium meyenii) whose names are, N-benzylpentadecanamide,N-benzylhexadecanamide, N-benzylheptadecanamide and N-benzyloctadecanamide, were studiedcombining the FTIR, FT-Raman and 1H and 13C-NMR spectroscopies with density functional theory (DFT)and ONION calculations. Furthermore, the N-benzylacetamide, N-benzylpropilamide and N-benzylhexanamide derivatives were also studied in order to compare their properties with those computed forthe four macamides. These seven N-benzylamides series have a common structure, C8H8NO-R, being Rthe side chain [e(CH2)neCH3] with a variable n number of CH2 groups. Here, the atomic charges, molecularelectrostatic potentials, stabilization energies, topological properties of those macamides wereanalyzed as a function of the number of C atoms of the side chain while the frontier orbitals were used tocompute the gap energies and some descriptors in order to predict their reactivities and behaviors infunction of the longitude of the side chain. Here, the force fields, the complete vibrational assignmentsand the corresponding force constants were only reported for N-benzylacetamide, N-benzyl hexanamideand N-benzylpentadecanamide due to the high number of vibration normal modes that present theremains macamides.