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Computational study of aromaticity, H-1 NMR spectra and intermolecular interactions of twisted thia-norhexaphyrin and its multiply annulated polypyrrolic derivatives
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Theoretical Chemistry and Biology.ORCID iD: 0000-0002-0716-3385
Natl Res Tomsk Polytech Univ, Res Sch Chem & Appl Biomed Sci, Lenin Ave 30, Tomsk 634050, Russia.;Univ Helsinki, Dept Chem, FIN-00014 Helsinki, Finland..ORCID iD: 0000-0002-2088-2608
East China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat & Joint Int Res Lab Precis Chem &, Shanghai 200237, Peoples R China..
East China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat & Joint Int Res Lab Precis Chem &, Shanghai 200237, Peoples R China..
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2019 (English)In: Physical Chemistry, Chemical Physics - PCCP, ISSN 1463-9076, E-ISSN 1463-9084, Vol. 21, no 45, p. 25334-25343Article in journal (Refereed) Published
Abstract [en]

The recently synthesized twisted thia-norhexaphyrin and its multiply annulated polypyrrolic derivatives have been studied computationally. Gauge-including magnetically induced current calculations predict a global nonaromatic character of the initial thia-norhexaphyrin due to the highly-twisted conformation of the macrocycle. Upon the oxidation of the thia-norhexaphyrin four multiply annulated polypyrrolic aromatic macrocycles are formed for which the global aromatic character is confirmed in agreement with experimentally measured H-1 NMR spectra. The calculation of the proton chemical shifts for the studied compounds by direct comparison with the tetramethylsilane standard leads to a significant mean absolute error. At the same time a linear regression procedure for the two selected groups of protons (CH and NH protons) provides much better values of calculated chemical shifts and tight correlation with experiment. The separate consideration of NH protons is motivated by the numerous intermolecular hydrogen bonds in which the protons are involved, which induce considerable upfield shifts, leading to a significant underestimation of the corresponding chemical shifts. Such a selected correlation can be used for accurate estimation of proton chemical shifts of the related porphyrinoids. Bader's theory of Atoms in Molecules has been applied for the studied twisted thia-norhexaphyrin and its multiply annulated polypyrrolic derivatives to characterize intramolecular H-bonds and other non-covalent interactions.

Place, publisher, year, edition, pages
ROYAL SOC CHEMISTRY , 2019. Vol. 21, no 45, p. 25334-25343
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Chemical Sciences
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URN: urn:nbn:se:kth:diva-267172DOI: 10.1039/c9cp04819gISI: 000506841300045PubMedID: 31701970Scopus ID: 2-s2.0-85075626181OAI: oai:DiVA.org:kth-267172DiVA, id: diva2:1391330
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QC 20200204

Available from: 2020-02-04 Created: 2020-02-04 Last updated: 2020-03-10Bibliographically approved

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Baryshnikov, Gleb V.Ågren, Hans

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