Silanols such as Et3SiOH and (3-ClC6H4)Si(CH3)2OH are acidic compounds with pka values of 13.6 and 11, respectively. Because of their greater acidity, silanols can be fully deprotonated in aqueous solution, especially the arylsilanols. The conjugate base is called a siloxide or a silanoate.
Since your amine is aryl amine (aniline derivatives), it might not be able to deprotonate the silanol since this amine is a very weak base. However, if you use an aryl amine derivative with a fairly good basicity you may be able to deprotonate the silanol. Other than the deprotonation reaction, no other reactions are expected to take place between R3Si-OH and Ar-NH2.
Beckmann, J.; Dakternieks, D.; Duthie, A.; Larchin, M. L.; Tiekink, E. R. T.: Tert-butoxysilanols as model compounds for labile key intermediates of the sol-gel process: crystal and molecular structures of (t-BuO)3SiOH and HO[(t-BuO)2SiO]2H, Appl. Organomet. Chem. 2003, 17, 52–62.
An abstract of paper on: Role of Amines in Adhesion of Polybutadiene to Glass Substrates. II. Reactions of Amines with Trimethoxysilanol and/or Fumed Silica. The Journal of Adhesion Volume 15, Issue 2, 1983. PreviewPDF Access optionsDOI:10.1080/00218468308073224
Y. Ecksteinab & P. Dreyfussapages 163-178.
Abstract
This paper is part of a larger investigation of the role of amines in the adhesion of polybutadiene to glass substrates. It describes near infrared, infrared and nuclear magnetic resonance spectroscopy studies of the interaction of amines with silanol groups usually under ambient conditions but sometimes when heated in air. Additional supporting evidence was obtained from gas liquid chromatography, mass spectrometry and elemental analyses. In order to assure a sufficiently high concentration of silanol groups, triethylsilanol and fused silica were used as models for the glass surface. The mechanism of interaction of aliphatic amines and of the aminosilane was different from that of aromatic amines. Most notably, reaction of aliphatic amines with carbon dioxide in the air and/or dissolved/adsorbed in/on the silanol occurred almost instantaneously, whereas the corresponding reaction of the aromatic amines with carbon dioxide was not observed under the experimental conditions used. The carbamates formed underwent further reactions much more rapidly than either the simple aromatic amines or the unmodified aliphatic amines.May give the answer.
The example paper you give does not report a direct reaction of aryl amine with Silanol. The reaction happens via the incorporation of CO2 to form the corresponding carbamat. No direct reaction between aryl amine and Silanols was documented.
The abstract that i provided describes near infrared, infrared and nuclear magnetic resonance spectroscopy studies of the interaction of amines with silanol groups usually under ambient conditions but sometimes when heated in air.
Thank you very much for your valuable notification.