Synthesis, characterization and theoretical calculations of model compounds of silanols catalyzed by TEMPO to elucidate the presence of Si–O–Si and Si–O–N bonds

Judith Percino; José A. Pacheco; Guillermo Soriano-Moro; Margarita Cerón; M. Eugenia Castro; Víctor M. Chapela; José Bonilla-Cruz; Tania E. Lara-Ceniceros; Mildred Flores-Guerrero; Enrique Saldivar-Guerra

doi:10.1039/C5RA10056A

Synthesis, characterization and theoretical calculations of model compounds of silanols catalyzed by TEMPO to elucidate the presence of Si–O–Si and Si–O–N bonds†

Judith Percino,*^a José A. Pacheco,^a Guillermo Soriano-Moro,^a Margarita Cerón,^a M. Eugenia Castro,^a Víctor M. Chapela,^a José Bonilla-Cruz,^b Tania E. Lara-Ceniceros,^b Mildred Flores-Guerrero^b and Enrique Saldivar-Guerra^c

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* Corresponding authors

^a Lab. de Polímeros, Centro de Química, Instituto de Ciencias, Benemérita Universidad Autónoma de Puebla, Complejo de Ciencias, ICUAP, Edif. 103H, 22 Sur y San Claudio, C.P. 72570 Puebla, Puebla, Mexico
E-mail: judith.percino@correo.buap.mx
Tel: +52-222-2295500 ext. 7285

^b Cento de Investigación en Materiales Avanzados S.C. (CIMAV-Unidad Monterrey), Alianza Norte 202, Autopista Monterrey-Aeropuerto Km 10, PIIT, C.P. 66600 Apodaca, Nuevo León, Mexico

^c Centro de Investigación en Química Aplicada, Blvd. Enrique Reyna No. 140, Col. San José de los Cerritos, C.P. 25294 Saltillo, Coahuila, Mexico

Abstract

We report the results from the reactions of 1-phenylethanol, 2-methylpropanol, trimethylsilanol and triphenylsilanol with TEMPO, OH-TEMPO and Br-TEMPO salt at different reaction conditions to obtain model functionalized compounds. With 1-phenylethanol, the ketone compound was obtained as expected, but when using triphenylsilanol the corresponding hexaphenyldisiloxane [di(triphenylsilane)ether] was obtained in crystal form, as well as the silaneoxiamine (Si–O–N). The hexaphenyldisiloxane crystal belonged to the triclinic crystal system with a space group P [1 with combining macron] , a = 8.5829(4) Å, b = 9.4856(4) Å, c = 10.9694(5) Å, α = 95.951(4)°, β = 90.059(3)°, γ = 113.352(4)°, the asymmetric unit comprised of Z = 1. The results showed that the synthetic method to obtain silane ether is simple and can be completed in one step, as well as independently of the type of TEMPO and base used. Also, under the same reactions conditions, we prepared the corresponding TEMPO-containing silanes as triphenylsilaneoxiamine and observed formation of Si-oxide chains through an in situ polycondensation reaction. The resulting compounds were characterized by FT-IR spectroscopy, mass spectrometry (EI), and ¹H-NMR. The best assignment for infrared spectroscopy characterization and the structural parameters by vibrational frequencies were determined by DFT calculations.

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Synthesis, characterization and theoretical calculations of model compounds of silanols catalyzed by TEMPO to elucidate the presence of Si–O–Si and Si–O–N bonds†

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Synthesis, characterization and theoretical calculations of model compounds of silanols catalyzed by TEMPO to elucidate the presence of Si–O–Si and Si–O–N bonds

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