nitrobenzene

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for nitrobenzene are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is nitrobenzene?

The molecule nitrobenzene presents a molecular formula of C6H5NO2 and its IUPAC name is nitrobenzene.

3D structure

Cartesian coordinates

Geometry of nitrobenzene in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

nitrobenzene LQNUZADURLCDLV-UHFFFAOYSA-N chemical compound 2D structure molecule svg
nitrobenzene

 

Molecule descriptors

 
IUPAC namenitrobenzene
InChI codeInChI=1S/C6H5NO2/c8-7(9)6-4-2-1-3-5-6/h1-5H
InChI KeyLQNUZADURLCDLV-UHFFFAOYSA-N
SMILESC1=CC=C(C=C1)[N+](=O)[O-]

Physico-Chemical properties

IUPAC namenitrobenzene
Molecular formulaC6H5NO2
Molecular weight123.11
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity
LogP
Topological polar surface area45.8

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.