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

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

10 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

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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Calix[n]triazoles and Related Conformational Studies

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