Skip to main content

6‐Chloro‐2‐oxindole: X‐ray and DFT‐calculated study

Buy Article:

$48.00 plus tax (Refund Policy)

Abstract:

The molecule of the title compound (systematic name: 6‐chloroindolin‐2‐one), C8H6ClNO, is almost planar, with a dihedral angle of 1.13 (9)° between the planes of the constituent pyrrolidine and benzene rings. Centrosymmetric dimers are formed in the crystal structure by N—H...O hydrogen bonds, and these dimers are additionally linked by Cl...Cl and C—H...O interactions. Density functional theory (DFT) calculations at the B3LYP/6‐31 G(d,p) level of theory were used to optimize the molecular structure and the geometry was best reproduced by optimization of two interacting molecules. The bond orders in the molecule, estimated using the natural bond orbitals (NBO) formalism, are consistent with the observed bond lengths. In particular, the contribution of the lone pair of electrons on the N atom to the N—C bond in the N—C=O group is revealed. The measured IR spectrum of the compound shows a red shift of the N—H stretching frequency compared with the free molecule, due to the formation of the hydrogen bonds.

Document Type: Research Article

DOI: http://dx.doi.org/10.1107/S0108270111038005

Publication date: October 15, 2011

bsc/ayc/2011/00000067/00000010/art00016
dcterms_title,dcterms_description,pub_keyword
6
5
20
40
5

Access Key

Free Content
Free content
New Content
New content
Open Access Content
Open access content
Subscribed Content
Subscribed content
Free Trial Content
Free trial content
Cookie Policy
X
Cookie Policy
ingentaconnect website makes use of cookies so as to keep track of data that you have filled in. I am Happy with this Find out more