1,2,4,5-Tetrazines vs. carboxylic acid dimers: Molecular chemistry vs. supramolecular chemistry

L Infantes, M F Mahon, L Male, P R Raithby, S L Teat, J Sauer, N Jagerovic, J Elguero, S Motherwell

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

The structures of six new tetrazines have been determined and their molecular packing has been compared to the supermolecular architecture observed in related carboxylic acid dimers. In the tetrazines, covalent N-N bonds are considered to replace the intermolecular O-(HO)-O-... hydrogen bonds of the carboxylic acids. In the systems investigated, it is apparent that, in the majority of cases, the covalent six-membered ring of the tetrazine is an appropriate replacement for the carboxylic acid synthon. This apparent interplay between molecular and supramolecular units may have applications in the crystal engineering of new materials.
Original languageEnglish
Pages (from-to)1205-1221
Number of pages17
JournalHelvetica Chimica Acta
Volume86
Issue number4
Publication statusPublished - 2003

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Supramolecular chemistry
Carboxylic Acids
Carboxylic acids
carboxylic acids
Dimers
dimers
chemistry
Crystal engineering
Hydrogen
Hydrogen bonds
engineering
hydrogen bonds
rings
crystals

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1,2,4,5-Tetrazines vs. carboxylic acid dimers: Molecular chemistry vs. supramolecular chemistry. / Infantes, L; Mahon, M F; Male, L; Raithby, P R; Teat, S L; Sauer, J; Jagerovic, N; Elguero, J; Motherwell, S.

In: Helvetica Chimica Acta, Vol. 86, No. 4, 2003, p. 1205-1221.

Research output: Contribution to journalArticle

Infantes, L, Mahon, MF, Male, L, Raithby, PR, Teat, SL, Sauer, J, Jagerovic, N, Elguero, J & Motherwell, S 2003, '1,2,4,5-Tetrazines vs. carboxylic acid dimers: Molecular chemistry vs. supramolecular chemistry', Helvetica Chimica Acta, vol. 86, no. 4, pp. 1205-1221.
Infantes, L ; Mahon, M F ; Male, L ; Raithby, P R ; Teat, S L ; Sauer, J ; Jagerovic, N ; Elguero, J ; Motherwell, S. / 1,2,4,5-Tetrazines vs. carboxylic acid dimers: Molecular chemistry vs. supramolecular chemistry. In: Helvetica Chimica Acta. 2003 ; Vol. 86, No. 4. pp. 1205-1221.
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AU - Infantes, L

AU - Mahon, M F

AU - Male, L

AU - Raithby, P R

AU - Teat, S L

AU - Sauer, J

AU - Jagerovic, N

AU - Elguero, J

AU - Motherwell, S

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AB - The structures of six new tetrazines have been determined and their molecular packing has been compared to the supermolecular architecture observed in related carboxylic acid dimers. In the tetrazines, covalent N-N bonds are considered to replace the intermolecular O-(HO)-O-... hydrogen bonds of the carboxylic acids. In the systems investigated, it is apparent that, in the majority of cases, the covalent six-membered ring of the tetrazine is an appropriate replacement for the carboxylic acid synthon. This apparent interplay between molecular and supramolecular units may have applications in the crystal engineering of new materials.

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JF - Helvetica Chimica Acta

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