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Synthesis and characterization of trichlorogermyl dioic acids: crystal structures and complementary hydrogen bonding motifs in 3-(trichlorogermyl) pentanedioic acid and 2-[(trichlorogermyl)methyl]butanedioic acid

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Abstract

A series of trichlorogermyl-substituted dicarboxylic acids of general formula HOOC–R′–COOH where R′=–CH2CH(GeCl3)CH2– 1, –CH(CH2GeCl3)CH2– 2, –CH(GeCl3)CH2– 3 and –CH(CH3)CH(GeCl3)– 4 were synthesized by the hydrogermylation reaction of unsaturated acids, such as trans-glutaconic (2-pentenedioic acid), itaconic (methylenebutanedioic acid), fumaric (2-butenedioic acid), and citraconic (2-methyl-2-butenedioic acid) acids with HGeCl3, which was produced in situ by the reaction of GeO2 with 37% HCl in presence of NaH2PO2 · H2O. All these compounds were characterized by melting point, CHN analysis, FTIR, and multinuclear NMR (1H; 13C; H,H-COSY). X-Ray crystal structures of 1 and 2 were analyzed to show supramolecular structures in which central Ge atom in each of these structures is four-coordinated with a slightly distorted tetrahedral geometry. Structurally, both compounds adopt supramolecular forms via strong intermolecular O–H–O interactions through 8-membered and 22-membered hydrogen bonded rings.

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Authors and Affiliations

  1. Department of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan

    Sumera Mahboob, Rohama Gill & Muhammad Mazhar

  2. Department of Chemistry, University of Bath, Bath, UK

    Gabriele Kociok-Köhn & Kieran C. Molloy

Authors
  1. Sumera Mahboob
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  2. Rohama Gill
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  3. Muhammad Mazhar
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  4. Gabriele Kociok-Köhn
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  5. Kieran C. Molloy
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Corresponding author

Correspondence to Muhammad Mazhar.

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Correspondence: Muhammad Mazhar, Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan.

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Mahboob, S., Gill, R., Mazhar, M. et al. Synthesis and characterization of trichlorogermyl dioic acids: crystal structures and complementary hydrogen bonding motifs in 3-(trichlorogermyl) pentanedioic acid and 2-[(trichlorogermyl)methyl]butanedioic acid. Monatsh Chem 139, 1019–1024 (2008). https://doi.org/10.1007/s00706-008-0880-x

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  • DOI: https://doi.org/10.1007/s00706-008-0880-x

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