CTED: the new aromaticity index based on corrected total electron density at bond critical points. (16th January 2014)

• Record Type: Journal Article
• Authors: Tokatlı, Ahmet; Ucun, Fatih
• Is Part Of: Journal of physical organic chemistry. Volume 27:Number 5(2014:May)
• Page Start: 380
• Page End: 386
• Publication Date: 2014-01-16
• Subjects: Chemistry, Physical organic -- Periodicals; 547.1
• DOI: 10.1002/poc.3274
• Languages: English
• ISSNs: 0894-3230

Abstract

<abstract abstract-type="main"> <title> <x xml:space="preserve">Abstract</x> </title> <p>In this work, the corrected total electron density <alternatives><inline-graphic mimetype="image" xlink:href="ark:/27927/pgg59w9b5kq" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /><mml:math altimg="urn:x-wiley:08943230:media:poc3274:poc3274-math-0001" display="inline" overflow="scroll" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mfenced close=")" open="("><mml:msubsup><mml:mi mathvariant="bold-italic">ρ</mml:mi><mml:mi mathvariant="bold-italic">BCP</mml:mi><mml:mi mathvariant="bold-italic">CTED</mml:mi></mml:msubsup></mml:mfenced></mml:math></alternatives> based on ellipticity (ε) at C–C bond critical points in a given ring and bond length alternations was introduced to estimate π‐electron density distributions in the ring. Then, to evaluate aromaticity of rings with any number of members, the <alternatives><inline-graphic mimetype="image" xlink:href="ark:/27927/pgg59w9b5j5" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /><mml:math altimg="urn:x-wiley:08943230:media:poc3274:poc3274-math-0002" display="inline" overflow="scroll" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:msubsup><mml:mi mathvariant="bold-italic">ρ</mml:mi><mml:mi mathvariant="bold-italic">BCP</mml:mi><mml:mi mathvariant="bold-italic">CTED</mml:mi></mml:msubsup></mml:math></alternatives> was normalized relative to a system assumed as a full aromatic, which is named as the corrected total electron density (CTED) aromaticity index. For a wide range of aromatic, nonaromatic and antiaromatic compounds, we have compared CTED index with the other commonly used aromatic indices, such as HOMA, PDI, FLU, NICS and recently introduced EL. CTED index was seen to be in agreement with the defined indices, and with general expectations. Hence, as similar to the other indices except from PDI, we have proposed that CTED index could be applied to study the aromaticity of rings without any restriction in the number of members of rings and used to analyze both the local and global aromatic character of rings as a new aromaticity index. Copyright © 2014 John Wiley & Sons, Ltd.</p> </abstract>