Sterically Crowded Heterocycles. I. Molecular Structure of 3-Chain Substituted 2-Phenylimidazo[1,2-a]pyridinium Salts

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Title:Sterically Crowded Heterocycles. I. Molecular Structure of 3-Chain Substituted 2-Phenylimidazo[1,2-a]pyridinium Salts
Creators:
Böhm, Stanislav
Kubík, Richard
Hradilek, Martin
Němeček, Jan
Hušák, Michal
Pakhomova, Svetlana
Ondráček, Jan
Kratochvíl, Bohumil
Kuthan, Josef
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 59, 12, pp. 2677-2690

Abstract

<p>2-Phenyl-3-[(<i>Z</i>)-1,3-diphenyl-3-oxopropenyl]imidazo[1,2-<i>a</i>]pyridine (<i>I</i>) was converted to corresponding 1-alkyl-2-phenyl-3-[(<i>Z</i>)-1,3-diphenyl-3-oxopropenyl]imidazo[1,2-<i>a</i>]pyridinium salts <i>III</i> - <i>VI</i> and 2-phenyl- 3-[(<i>Z</i>)-1,3-diphenyl-3-oxopropenyl]imidazo[1,2-<i>a</i>]pyridinium perchlorate (<i>VII</i>). The protonation site is discussed in terms of calculated molecular energies of alternative cations. The X-ray structure analyses of enone <i>I</i> and its quaternary periodide <i>III</i> are reported and compared with the PM3 molecular optimizations. <sup>1</sup>H NMR and <sup>13</sup>C NMR spectra reveal well changes of molecular structures caused by the transformation of the base <i>I</i> into salts <i>III</i> - <i>VII</i>.

Title:Sterically Crowded Heterocycles. I. Molecular Structure of 3-Chain Substituted 2-Phenylimidazo[1,2-a]pyridinium Salts
Creators:
Böhm, Stanislav
Kubík, Richard
Hradilek, Martin
Němeček, Jan
Hušák, Michal
Pakhomova, Svetlana
Ondráček, Jan
Kratochvíl, Bohumil
Kuthan, Josef
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:59
Number:12
Page Range:pp. 2677-2690
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19942677UNSPECIFIED
ID Code:686
Item Type:Article
Deposited On:06 Feb 2009 17:03
Last Modified:06 Feb 2009 16:03

Citation

Böhm, Stanislav; Kubík, Richard; Hradilek, Martin; Němeček, Jan; Hušák, Michal; Pakhomova, Svetlana; Ondráček, Jan; Kratochvíl, Bohumil; Kuthan, Josef (1994) Sterically Crowded Heterocycles. I. Molecular Structure of 3-Chain Substituted 2-Phenylimidazo[1,2-a]pyridinium Salts. Collection of Czechoslovak Chemical Communications, 59 (12). pp. 2677-2690. ISSN 0010-0765

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