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Chirality recognition in dimers of tetrahydro-2-furoic acid (THFA), a biologically active carboxylic acid, was studied in a conformer-specific manner using rotational spectroscopy and theoretical approaches. The THFA monomer is known to have a strong preference for the trans - over the cis -COOH configuration. Two drastically different scenarios are possible for the detectable THFA dimer the kinetically controlled formation of a dimer bound by feeble interactions between two trans subunits or the thermodynamically controlled formation of