Nanostructured TiO2(B) thin films were found to have strong and fast chemiresistive response to nitro-aromatic and nitro-amino explosives recently. In this study, the effects of dipole moment and electron deficiency of the analyte molecules on the chemiresistive response are explored to understand the details of molecular interactions of analytes with the sensor surface which lead to charge depletion and the chemiresistive effect. It was found that the speed of the response is dominated by the polarity of the analytes and molecules with larger dipole moments produce faster responses. The degree of the response was found to be dominated by the electron deficiency of the analytes and molecules with greater electron deficiency produce stronger chemiresistive responses.