Tautomerism-Induced Cis–Trans Isomerization of Pyridylethenyl N-Confused Porphyrin

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dc.contributor.author Sakashita, Ryuichi
dc.contributor.author Oka, Yasutaka
dc.contributor.author Akimaru, Hisanori
dc.contributor.author Kesavan, Praseetha E.
dc.contributor.author Ishida, Masatoshi
dc.contributor.author Toganoh, Motoki
dc.contributor.author Ishizuka, Tomoya
dc.contributor.author Mori, Shigeki
dc.contributor.author Furuta, Hiroyuki
dc.coverage.spatial US
dc.date.accessioned 2017-10-10T13:03:43Z
dc.date.available 2017-10-10T13:03:43Z
dc.date.issued 2017-08
dc.identifier.citation Sakashita, Ryuichi; Oka, Yasutaka; Akimaru, Hisanori;Kesavan, Praseetha E.; Ishida, Masatoshi; Toganoh, Motoki; Ishizuka, Tomoya; Mori, Shigeki and Furuta, Hiroyuki, “Tautomerism-Induced Cis–Trans Isomerization of Pyridylethenyl N-Confused Porphyrin”, The Journal of Organic Chemistry, DOI: 10.1021/acs.joc.7b01770, vol. 82, no. 16, pp. 8686-8696, Aug. 2017. en_US
dc.identifier.issn 0022-3263
dc.identifier.issn 1520-6904
dc.identifier.uri https://repository.iitgn.ac.in/handle/123456789/3180
dc.identifier.uri http://dx.doi.org/10.1021/acs.joc.7b01770
dc.description.abstract Pyridylethenyl-substituted N-confused porphyrins (NCPs) were synthesized, and their cis–trans isomerization was studied. Among four possible isomers, trans-3H and cis-2H types of structures, of which aromaticity and absorption/emission properties differ largely, were isolated. The cis-isomer was largely stabilized by the intramolecular hydrogen bonding between the pyrrolic-NH and the pyridinic-N in the vicinity. The thermal cis–trans isomerization proceeded even at 30 °C, which was significantly accelerated by the pyridine added to the system. The kinetic studies revealed that the isomerization reaction was second-order and the activation energy of the thermal isomerization from cis to trans isomer was ΔG0⧧cis→trans = 35.7 kcal/mol at 298 K, which is significantly smaller than that of Ni complex (42.3 kcal/mol). An intermolecular proton transfer induced cis–trans isomerization mechanism was proposed. en_US
dc.description.statementofresponsibility by Ryuichi Sakashita, Yasutaka Oka, Hisanori Akimaru, Praseetha E. Kesavan, Masatoshi Ishida, Motoki Toganoh, Tomoya Ishizuka, Shigeki Mori and Hiroyuki Furuta
dc.format.extent Vol.82, no. 16, pp. 8686-8696
dc.language.iso en en_US
dc.publisher ACS Publication
dc.title Tautomerism-Induced Cis–Trans Isomerization of Pyridylethenyl N-Confused Porphyrin en_US
dc.type Article en_US
dc.relation.journal Journal of Organic Chemistry


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