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Tunable chiral triazole-based halogen bond donors: assessment of donor strength in solution with nitrogen-containing acceptors.

ABSTRACT: Strong halogen bond (XB) donors are needed for the activation of neutral substrates. We demonstrate that XB donor properties of iodo-triazoles can be significantly enhanced by quaternization in combination with varying the counterion and aromatic substituent, exemplified by association constants with quinuclidine as high as 1.1 × 10⁴ M^-1.

SUBMITTER: Peterson A

PROVIDER: S-EPMC9063393 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature

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Tunable chiral triazole-based halogen bond donors: assessment of donor strength in solution with nitrogen-containing acceptors.

Peterson Anna A Kaasik Mikk M Metsala Andrus A Järving Ivar I Adamson Jasper J Kanger Tõnis T

RSC advances 20190415 21

Strong halogen bond (XB) donors are needed for the activation of neutral substrates. We demonstrate that XB donor properties of iodo-triazoles can be significantly enhanced by quaternization in combination with varying the counterion and aromatic substituent, exemplified by association constants with quinuclidine as high as 1.1 × 10<sup>4</sup> M<sup>-1</sup>. ...[more]

PMID: 35517004

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