Journal of Organic & Inorganic Chemistry

Raman Characterization of Phenyl-Derivatives: From Primary Amine to Diazonium Salts

The objective of the present work is to use Raman spectroscopy for characterizing, the fate of phenyl-derivatives, from phenyl-amines to aryl-diazonium derivatives (ADD). Four ADD were investigated: (i) benzene diazoniumtetrafluoroborate (DS), (ii) 4-decyl benzene diazoniumtetrafluoroborate (DS-C₁₀H₂₁), (iii) 4-carboxybenzene diazoniumtetrafluoroborate (DS-COOH) and (iv) 4-(aminoethyl) benzene diazoniumtetrafluoroborate (DS-(CH₂)₂NH₂). Raman investigation of the above ADD confirmed the existence of an N≡N bond stretching in the range of 2285-2305 cm^-1. Moreover, the strong band related to CH in plane-bending and C-N-stretching modes in the 1073-1080 cm^-1 range, is a signature of phenyl derivatives stemming from ADD. Furthermore, we analyzed and discuss the H-N- (ring) symmetric stretching modes and the ring-N, as well as the benzene-ring vibrational modes, the C-H related vibrations and the functions in para-position carried by the aromatic ring. The effect of structural changes, the conformational rearrangements from amines to ADD and the influence of the substituent located in the para-position on Raman modes, were examined as well. Finally, Raman experiments supported by Density Functional Theory (DFT) modeling allowed us to determine the crystalline structure of DS-COOH.

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Author(s):

Betelu S, Tijunelyte I, Boubekeur-Lecaque L, Ignatiadis I, Schnepf AC, Guenin E, Bouchemal N, Felidj N, Rinnert E and Lamy de la Chapelle M

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