Formyl- and acetylindols: Vibrational spectroscopy of an expectably pharmacologically active compound family

• Published in: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy Vol. 74; no. 5; pp. 1031 - 1045
• Main Authors: Billes, Ferenc, Podea, Paula Veronica, Mohammed-Ziegler, Ildikó, Toşa, Monica, Mikosch, Hans, Irimie, Dan-Florin
• Format: Journal Article
• Language: English
• Published: England Elsevier B.V 01-12-2009
• Subjects: Acetyl; Computer Simulation; Formyl; FT-IR; Indole derivatives; Indoles - chemistry; Molecular Conformation; Normal coordinate analysis; Raman; Spectrophotometry, Infrared; Spectrum Analysis, Raman; Vibration; FT-IR; Acetyl; Normal coordinate analysis; Raman; Formyl; Indole derivatives
• ISSN: 1386-1425; 1873-3557
• DOI: 10.1016/j.saa.2009.08.044

In the peresent paper, indole and its seven derivatives were compared, namely 3-formylindole, 1-methyl-3-formylindole, 1-ethyl-3-formylindole, 3-acetylindole, 1-methyl-3-acetylindole, 1-ethyl-3-acetylindole and 1,3-diacetylindole. The substitution of indole in position 3 with aldehydes and with alkyl groups cause only minor changes in the molecular geometry, however, substantially larger alterations are found in the charge distribution and in the vibrational force constants. The appearance of the aldhyde groups increased the degree of association as it was observable on the shape of infrared NH stretching band and its shifts. The alkyl substitution shifts the aldehyde carbonyl stretch band frequencies to somewhat higher values. The effect of the second acetyl group in position 1 is not comparable with those of the 1-alkyl groups. The latter effect is observable in the molecular geometry, however, it is more pronounced in the changes of the net charge distribution, the vibrational force constants and the infrared spectra.