New Calix[4]arene-Based Amides - Their Synthesis, Conformation, Complexation

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Title:New Calix[4]arene-Based Amides - Their Synthesis, Conformation, Complexation
Creators:
Stibor, Ivan
Růžičková, Martina
Krátký, Rostislav
Vindyš, Michal
Havlíček, Jaroslav
Pinkhassik, Evguenni
Lhoták, Pavel
Mustafina, Asiya R.
Morozova, Yuliya E.
Kazakova, Ella Kh.
Gubskaya, Valentina P.
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 66, 4, pp. 641-662
Uncontrolled Keywords:Calix[4]arenes, Calixarenes, Conformation analysis, X-Ray diffraction, Receptors, Complexation, Recognition, NMR spectroscopy

Abstract

New chiral calix[4]arene-based diol-diamides <strong>1a</strong>, <strong>1b</strong>, tetraamides <strong>2a</strong>, <strong>2b</strong> and <strong>7</strong> as well as achiral diamide <strong>3</strong> and tetraamides <strong>4</strong>-<strong>6</strong> were prepared. The conformation of <strong>1</strong> has been studied in solution by NMR and in solid state by X-ray crystallography. The pinched-cone conformation of the calix[4]arene skeleton in <strong>1</strong> was found to be stabilized by a circular array of hydrogen bonds formed by two phenolic O-H and two amidic N-H bonds at lower rim. Whereas no significant complexation of Na<sup>+</sup> was observed in solution for diamides <strong>1</strong> and <strong>3</strong>, tetraamides <strong>2</strong>, <strong>4</strong>, <strong>5</strong>, and <strong>6</strong> give strong complexes with Na<sup>+</sup> as confirmed by NMR titrations of <strong>2</strong> and <strong>4</strong>. The influence of anions and the solvents used on complexation ability of <strong>2</strong> towards Na<sup>+</sup> is negligible. <p>

Title:New Calix[4]arene-Based Amides - Their Synthesis, Conformation, Complexation
Creators:
Stibor, Ivan
Růžičková, Martina
Krátký, Rostislav
Vindyš, Michal
Havlíček, Jaroslav
Pinkhassik, Evguenni
Lhoták, Pavel
Mustafina, Asiya R.
Morozova, Yuliya E.
Kazakova, Ella Kh.
Gubskaya, Valentina P.
Uncontrolled Keywords:Calix[4]arenes, Calixarenes, Conformation analysis, X-Ray diffraction, Receptors, Complexation, Recognition, NMR spectroscopy
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:66
Number:4
Page Range:pp. 641-662
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20010641UNSPECIFIED
ID Code:1817
Item Type:Article
Deposited On:06 Feb 2009 17:12
Last Modified:06 Feb 2009 16:13

Citation

Stibor, Ivan; Růžičková, Martina; Krátký, Rostislav; Vindyš, Michal; Havlíček, Jaroslav; Pinkhassik, Evguenni; Lhoták, Pavel; Mustafina, Asiya R.; Morozova, Yuliya E.; Kazakova, Ella Kh.; Gubskaya, Valentina P. (2001) New Calix[4]arene-Based Amides - Their Synthesis, Conformation, Complexation. Collection of Czechoslovak Chemical Communications, 66 (4). pp. 641-662. ISSN 0010-0765

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