First X-ray structural characterisation of host-guest interactions in tetra-tetrazole macrocycles

Andrew D. Bond; Adrienne Fleming; Jackie Gaire; Fintan Kelleher; John McGinley; Vickie McKee

doi:10.1016/j.tet.2009.07.063

First X-ray structural characterisation of host-guest interactions in tetra-tetrazole macrocycles

Andrew D. Bond
, Adrienne Fleming
, Jackie Gaire
, Fintan Kelleher
, John McGinley
, Vickie McKee

School of Chemical and BioPharmaceutical Science

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

Abstract

The syntheses of tetra-tetrazole macrocycles, containing two 1,3-bis(tetrazole)benzene units linked by a variety of n-alkyl (n=3, 5, 7 or 9 carbon atoms) chain lengths, are described. The crystal structures of two 1,3-bis(tetrazole)benzenes containing pendant bromoalkyl chains (n=3 or 5) are reported. A tetra-tetrazole macrocycle has also been structurally characterised and contains an unexpected 'host-guest' interaction through binding of a chloroform solvent molecule. The resulting deviation of the macrocycle from planarity results from a combination of the 'host-guest' interaction and strong intermolecular interactions between adjacent tetrazole and phenylene rings.

Original language	English
Pages (from-to)	7942-7947
Number of pages	6
Journal	Tetrahedron
Volume	65
Issue number	38
DOIs	https://doi.org/10.1016/j.tet.2009.07.063
Publication status	Published - 19 Sep 2009

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10.1016/j.tet.2009.07.063

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title = "First X-ray structural characterisation of host-guest interactions in tetra-tetrazole macrocycles",

abstract = "The syntheses of tetra-tetrazole macrocycles, containing two 1,3-bis(tetrazole)benzene units linked by a variety of n-alkyl (n=3, 5, 7 or 9 carbon atoms) chain lengths, are described. The crystal structures of two 1,3-bis(tetrazole)benzenes containing pendant bromoalkyl chains (n=3 or 5) are reported. A tetra-tetrazole macrocycle has also been structurally characterised and contains an unexpected 'host-guest' interaction through binding of a chloroform solvent molecule. The resulting deviation of the macrocycle from planarity results from a combination of the 'host-guest' interaction and strong intermolecular interactions between adjacent tetrazole and phenylene rings.",

author = "Bond, \{Andrew D.\} and Adrienne Fleming and Jackie Gaire and Fintan Kelleher and John McGinley and Vickie McKee",

note = "Funding Information: We thank the Postgraduate R\&D Skills programme (Technological Sector Research, Strand I, Project Code CRS/01/TA02) for financial assistance. A.D.B. is grateful to the Danish Natural Sciences Research Council and the Carlsberg Foundation for provision of the X-ray equipment. ",

year = "2009",

month = sep,

day = "19",

doi = "10.1016/j.tet.2009.07.063",

language = "English",

volume = "65",

pages = "7942--7947",

journal = "Tetrahedron",

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publisher = "Elsevier Ltd.",

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TY - JOUR

T1 - First X-ray structural characterisation of host-guest interactions in tetra-tetrazole macrocycles

AU - Bond, Andrew D.

AU - Fleming, Adrienne

AU - Gaire, Jackie

AU - Kelleher, Fintan

AU - McGinley, John

AU - McKee, Vickie

N1 - Funding Information: We thank the Postgraduate R&D Skills programme (Technological Sector Research, Strand I, Project Code CRS/01/TA02) for financial assistance. A.D.B. is grateful to the Danish Natural Sciences Research Council and the Carlsberg Foundation for provision of the X-ray equipment.

PY - 2009/9/19

Y1 - 2009/9/19

N2 - The syntheses of tetra-tetrazole macrocycles, containing two 1,3-bis(tetrazole)benzene units linked by a variety of n-alkyl (n=3, 5, 7 or 9 carbon atoms) chain lengths, are described. The crystal structures of two 1,3-bis(tetrazole)benzenes containing pendant bromoalkyl chains (n=3 or 5) are reported. A tetra-tetrazole macrocycle has also been structurally characterised and contains an unexpected 'host-guest' interaction through binding of a chloroform solvent molecule. The resulting deviation of the macrocycle from planarity results from a combination of the 'host-guest' interaction and strong intermolecular interactions between adjacent tetrazole and phenylene rings.

AB - The syntheses of tetra-tetrazole macrocycles, containing two 1,3-bis(tetrazole)benzene units linked by a variety of n-alkyl (n=3, 5, 7 or 9 carbon atoms) chain lengths, are described. The crystal structures of two 1,3-bis(tetrazole)benzenes containing pendant bromoalkyl chains (n=3 or 5) are reported. A tetra-tetrazole macrocycle has also been structurally characterised and contains an unexpected 'host-guest' interaction through binding of a chloroform solvent molecule. The resulting deviation of the macrocycle from planarity results from a combination of the 'host-guest' interaction and strong intermolecular interactions between adjacent tetrazole and phenylene rings.

UR - https://www.scopus.com/pages/publications/68549110319

U2 - 10.1016/j.tet.2009.07.063

DO - 10.1016/j.tet.2009.07.063

M3 - Article

AN - SCOPUS:68549110319

SN - 0040-4020

VL - 65

SP - 7942

EP - 7947

JO - Tetrahedron

JF - Tetrahedron

IS - 38

ER -

First X-ray structural characterisation of host-guest interactions in tetra-tetrazole macrocycles

Abstract

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