Experimental investigation of halogen-bond hard-soft acid-base complementarity

Asia Marie S. Riel; Morly J. Jessop; Daniel A. Decato; Casey J. Massena; Vinicius R. Nascimento; Orion B. Berryman

doi:10.1107/S2052520617001809

Experimental investigation of halogen-bond hard-soft acid-base complementarity

Asia Marie S. Riel, Morly J. Jessop, Daniel A. Decato, Casey J. Massena, Vinicius R. Nascimento, Orion B. Berryman

Chemistry

University of Montana

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

21 Scopus citations

Abstract

The halogen bond (XB) is a topical noncovalent interaction of rapidly increasing importance. The XB employs a 'soft' donor atom in comparison to the 'hard' proton of the hydrogen bond (HB). This difference has led to the hypothesis that XBs can form more favorable interactions with 'soft' bases than HBs. While computational studies have supported this suggestion, solution and solid-state data are lacking. Here, XB soft-soft complementarity is investigated with a bidentate receptor that shows similar associations with neutral carbonyls and heavy chalcogen analogs. The solution speciation and XB soft-soft complementarity is supported by four crystal structures containing neutral and anionic soft Lewis bases. Investigation of halogen-bond hard-soft acid-base complementarity in solution and solid-phases is presented.

Original language	English
Pages (from-to)	203-209
Number of pages	7
Journal	Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials
Volume	73
Issue number	2
DOIs	https://doi.org/10.1107/S2052520617001809
State	Published - Apr 1 2017

Keywords

NMR titration
anion recognition
halogen bonding
hard-soft acid-base

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10.1107/S2052520617001809

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title = "Experimental investigation of halogen-bond hard-soft acid-base complementarity",

abstract = "The halogen bond (XB) is a topical noncovalent interaction of rapidly increasing importance. The XB employs a 'soft' donor atom in comparison to the 'hard' proton of the hydrogen bond (HB). This difference has led to the hypothesis that XBs can form more favorable interactions with 'soft' bases than HBs. While computational studies have supported this suggestion, solution and solid-state data are lacking. Here, XB soft-soft complementarity is investigated with a bidentate receptor that shows similar associations with neutral carbonyls and heavy chalcogen analogs. The solution speciation and XB soft-soft complementarity is supported by four crystal structures containing neutral and anionic soft Lewis bases. Investigation of halogen-bond hard-soft acid-base complementarity in solution and solid-phases is presented.",

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AU - Riel, Asia Marie S.

AU - Jessop, Morly J.

AU - Decato, Daniel A.

AU - Massena, Casey J.

AU - Nascimento, Vinicius R.

AU - Berryman, Orion B.

N1 - Publisher Copyright: © International Union of Crystallography, 2017.

PY - 2017/4/1

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N2 - The halogen bond (XB) is a topical noncovalent interaction of rapidly increasing importance. The XB employs a 'soft' donor atom in comparison to the 'hard' proton of the hydrogen bond (HB). This difference has led to the hypothesis that XBs can form more favorable interactions with 'soft' bases than HBs. While computational studies have supported this suggestion, solution and solid-state data are lacking. Here, XB soft-soft complementarity is investigated with a bidentate receptor that shows similar associations with neutral carbonyls and heavy chalcogen analogs. The solution speciation and XB soft-soft complementarity is supported by four crystal structures containing neutral and anionic soft Lewis bases. Investigation of halogen-bond hard-soft acid-base complementarity in solution and solid-phases is presented.

AB - The halogen bond (XB) is a topical noncovalent interaction of rapidly increasing importance. The XB employs a 'soft' donor atom in comparison to the 'hard' proton of the hydrogen bond (HB). This difference has led to the hypothesis that XBs can form more favorable interactions with 'soft' bases than HBs. While computational studies have supported this suggestion, solution and solid-state data are lacking. Here, XB soft-soft complementarity is investigated with a bidentate receptor that shows similar associations with neutral carbonyls and heavy chalcogen analogs. The solution speciation and XB soft-soft complementarity is supported by four crystal structures containing neutral and anionic soft Lewis bases. Investigation of halogen-bond hard-soft acid-base complementarity in solution and solid-phases is presented.

KW - NMR titration

KW - anion recognition

KW - halogen bonding

KW - hard-soft acid-base

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JO - Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials

JF - Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials

IS - 2

ER -

Experimental investigation of halogen-bond hard-soft acid-base complementarity

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Keywords

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