Calix[n]triazoles and Related Conformational Studies

Illan Kim; Kyoung Chul Ko; Woo Ram Lee; Jihee Cho; Jong Hun Moon; Dohyun Moon; Amit Sharma; Jin Yong Lee; Jong Seung Kim; Sanghee Kim

doi:10.1021/acs.orglett.7b02557

Calix[n]triazoles and Related Conformational Studies

Illan Kim
, Kyoung Chul Ko
, Woo Ram Lee
, Jihee Cho
, Jong Hun Moon
, Dohyun Moon
, Amit Sharma
, Jin Yong Lee^*
, Jong Seung Kim
, Sanghee Kim

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

16 Citations (Scopus)

Abstract

Calix[n]triazoles are developed as new derivatives in the calixarene family. Calixtriazole compounds 2-4 are synthesized using an iterative convergent strategy including an inter-/intramolecular copper(I)-catalyzed azide-alkyne cycloaddition reaction. Solid-state structures are clearly refined to give 1,2-alternate and partial cone conformations for calix[4]triazole and calix[5]triazole, respectively. Theoretical studies based on density functional theory (DFT) calculations indicated that intermolecular interactions are crucial in determining the conformers of the crystals, and the most stable conformers of calix[4]triazole, calix[5]triazole, and calix[6]triazole in the monomeric forms are 1,3-alternate, 1,3-alternate, and 1,3,5-alternate, respectively.

Original language	English
Pages (from-to)	5509-5512
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	20
DOIs	https://doi.org/10.1021/acs.orglett.7b02557
Publication status	Published - 2017 Oct 20

Bibliographical note

Funding Information:
This research was supported by 2016R1A2A1A05005375 (S.K.), Nos. 2009-0081566 and 2010-0020209 (J.S.K.), and NRF-2017R1C1B5018060 (W.R.L.) of National Research Foundation (NRF) grant funded by the Ministry of Science, ICT & Future Planning (MSIP) of Korea. This work was also supported by No. KSC-2016-C3-0070 (J.Y.L.) of the supercomputing application research of KISTI supercomputing center.

Publisher Copyright:
© 2017 American Chemical Society.

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Calix[n]triazoles and Related Conformational Studies",

abstract = "Calix[n]triazoles are developed as new derivatives in the calixarene family. Calixtriazole compounds 2-4 are synthesized using an iterative convergent strategy including an inter-/intramolecular copper(I)-catalyzed azide-alkyne cycloaddition reaction. Solid-state structures are clearly refined to give 1,2-alternate and partial cone conformations for calix[4]triazole and calix[5]triazole, respectively. Theoretical studies based on density functional theory (DFT) calculations indicated that intermolecular interactions are crucial in determining the conformers of the crystals, and the most stable conformers of calix[4]triazole, calix[5]triazole, and calix[6]triazole in the monomeric forms are 1,3-alternate, 1,3-alternate, and 1,3,5-alternate, respectively.",

author = "Illan Kim and Ko, \{Kyoung Chul\} and Lee, \{Woo Ram\} and Jihee Cho and Moon, \{Jong Hun\} and Dohyun Moon and Amit Sharma and Lee, \{Jin Yong\} and Kim, \{Jong Seung\} and Sanghee Kim",

note = "Funding Information: This research was supported by 2016R1A2A1A05005375 (S.K.), Nos. 2009-0081566 and 2010-0020209 (J.S.K.), and NRF-2017R1C1B5018060 (W.R.L.) of National Research Foundation (NRF) grant funded by the Ministry of Science, ICT \& Future Planning (MSIP) of Korea. This work was also supported by No. KSC-2016-C3-0070 (J.Y.L.) of the supercomputing application research of KISTI supercomputing center. Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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AU - Kim, Illan

AU - Ko, Kyoung Chul

AU - Lee, Woo Ram

AU - Cho, Jihee

AU - Moon, Jong Hun

AU - Moon, Dohyun

AU - Sharma, Amit

AU - Lee, Jin Yong

AU - Kim, Jong Seung

AU - Kim, Sanghee

N1 - Funding Information: This research was supported by 2016R1A2A1A05005375 (S.K.), Nos. 2009-0081566 and 2010-0020209 (J.S.K.), and NRF-2017R1C1B5018060 (W.R.L.) of National Research Foundation (NRF) grant funded by the Ministry of Science, ICT & Future Planning (MSIP) of Korea. This work was also supported by No. KSC-2016-C3-0070 (J.Y.L.) of the supercomputing application research of KISTI supercomputing center. Publisher Copyright: © 2017 American Chemical Society.

PY - 2017/10/20

Y1 - 2017/10/20

N2 - Calix[n]triazoles are developed as new derivatives in the calixarene family. Calixtriazole compounds 2-4 are synthesized using an iterative convergent strategy including an inter-/intramolecular copper(I)-catalyzed azide-alkyne cycloaddition reaction. Solid-state structures are clearly refined to give 1,2-alternate and partial cone conformations for calix[4]triazole and calix[5]triazole, respectively. Theoretical studies based on density functional theory (DFT) calculations indicated that intermolecular interactions are crucial in determining the conformers of the crystals, and the most stable conformers of calix[4]triazole, calix[5]triazole, and calix[6]triazole in the monomeric forms are 1,3-alternate, 1,3-alternate, and 1,3,5-alternate, respectively.

AB - Calix[n]triazoles are developed as new derivatives in the calixarene family. Calixtriazole compounds 2-4 are synthesized using an iterative convergent strategy including an inter-/intramolecular copper(I)-catalyzed azide-alkyne cycloaddition reaction. Solid-state structures are clearly refined to give 1,2-alternate and partial cone conformations for calix[4]triazole and calix[5]triazole, respectively. Theoretical studies based on density functional theory (DFT) calculations indicated that intermolecular interactions are crucial in determining the conformers of the crystals, and the most stable conformers of calix[4]triazole, calix[5]triazole, and calix[6]triazole in the monomeric forms are 1,3-alternate, 1,3-alternate, and 1,3,5-alternate, respectively.

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ER -

Calix[n]triazoles and Related Conformational Studies

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