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

Type Article
Date 2017
Language English
Other localization http://organic-inorganic.imedpub.com/abstract/raman-characterization-ofrnphenylderivatives-from-primaryrnamine-to-diazonium-salts-19072.html
Author(s) Betelu S1, Tijunelyte I2, Boubekeur Lecaque L3, Ignatiadis I, Schnepf Ac1, Guenin E2, Bouchemal N2, Felidj N3, Rinnert EmmanuelORCID4, Lamy De La Chapelle M2
Affiliation(s) 1 : BRGM, Water Environment and Eco- Technology Division, F-45060 Orléans Cedex 02, France
2 : University Paris 13, Sorbonne Paris Cité, CSPBAT laboratory, UMR 7244 CNRS, UFR SMBH, 74, Rue Marcel Cachin, 93017 Bobigny, France
3 : University Paris Diderot, Sorbonne Paris Cité, ITODYS, UMR 7086 CNRS, 15 rue J-A de Baïf, 75205 Paris Cedex 13, France
4 : IFREMER, Brittany Center, Measurements, Detection and Sensors Laboratory, CS10070, 29280 Plouzané, France
Source Journal of Organic & Inorganic Chemistry (2472-1123) (iMedPub Journals), 2017 , Vol. 3 , N. 1 , P. 1-10
DOI 10.21767/2472-1123.100021
Keyword(s) Phenyl-amines, Diazonium salts, Synthesis and characterization, Raman, DFT calculations

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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Betelu S, Tijunelyte I, Boubekeur Lecaque L, Ignatiadis I, Schnepf Ac, Guenin E, Bouchemal N, Felidj N, Rinnert Emmanuel, Lamy De La Chapelle M (2017). Raman Characterization of Phenyl-Derivatives: From Primary Amine to Diazonium Salts. Journal of Organic & Inorganic Chemistry, 3(1), 1-10. Publisher's official version : https://doi.org/10.21767/2472-1123.100021 , Open Access version : https://archimer.ifremer.fr/doc/00391/50262/