Calculation of magnetic response properties of tetrazines

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http://hdl.handle.net/10138/316272

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Orozco-Ic , M , Celaya , C A & Sundholm , D 2020 , ' Calculation of magnetic response properties of tetrazines ' , RSC Advances , vol. 10 , no. 31 , pp. 18124-18130 . https://doi.org/10.1039/d0ra01641a

Title: Calculation of magnetic response properties of tetrazines
Author: Orozco-Ic, Mesias; Celaya, Christian A.; Sundholm, Dage
Contributor: University of Helsinki, Department of Chemistry
University of Helsinki, Department of Chemistry
Date: 2020-05-13
Language: eng
Number of pages: 7
Belongs to series: RSC Advances
ISSN: 2046-2069
URI: http://hdl.handle.net/10138/316272
Abstract: Magnetic response properties of 1,2,3,5-tetrazine derivatives including the newly synthesized 4,6-diphenyl-1,2,3,5-tetrazine have been studied computationally at the density functional theory (DFT) level. Calculations of magnetically induced current densities and induced magnetic fields show that the unsubstituted 1,2,3,5-tetrazine is almost as aromatic as benzene. Separating the magnetic shielding functions into molecular orbital components provided additional insights into the magnetic response. The aromatic character estimated from magnetically induced current densities and induced magnetic fields shows that NICS pi zz(0) values and ring-current strengths yield about the same degree of aromaticity, whereas NICSzz(0) and NICSzz(1) values are contaminated by sigma electron contributions. The studied 1,2,3,5-tetrazine derivatives are less aromatic than the unsubstituted one. Calculations of magnetic response properties of 4,6-diphenyl-1,2,3,5-tetrazine showed that it is the least aromatic among the studied molecules according to the ring-current criterion, while 4,6-[1,2,3,5]-ditetrazinyl-1,2,3,5-tetrazine is as aromatic as 4,6-dimethyl-1,2,3,5-tetrazine and slightly less aromatic than the unsubstituted 1,2,3,5-tetrazine.
Subject: INDEPENDENT CHEMICAL-SHIFTS
RING CURRENTS
QUANTUM CONTRIBUTIONS
CURRENT DENSITIES
ORBITAL ANALYSIS
BASIS-SETS
BENZENE
AROMATICITY
NICS
PI
116 Chemical sciences
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