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| - Formation of Hydrogen-Bonded Structures in Jet-Cooled Complexes of a ChiralChromophore Studied by IR/UV Double Resonance Spectroscopy: DiastereoisomericComplexes of (±)-2-Naphthyl-1-ethanol with (±)-2-Amino-1-propanol
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| - The structure of weakly bound diastereoisomeric complexes of (±)-2-naphthyl-1-ethanol with (±)-2-amino-1-propanol (alaninol) has been interrogated by means of laser-induced fluorescence and IR fluorescence dipspectroscopy. The diastereoisomers have been discriminated on the basis of the complexation-induced shiftof the S0−S1 transition of the chromophore. The heterochiral complex exists under one dominant fluorescentform, while two isomers have been detected for the homochiral complex, with a dramatically differentspectroscopic signature in the ν(OH) region. The solely observed heterochiral complex involves an OH···Obond from the chromophore to alaninol, with a quasi retention of the most stable structure of the aminoalcohol molecule (intramolecular hydrogen bond). One of the homochiral isomers adopts the same OH···Ostructure while the second homochiral one involves a OH···N bond to alaninol, whose conformation differsfrom that of the most stable isolated fragment (absence of the intramolecular hydrogen bond). The observationof both structures of the homochiral complex leaves no doubt as to the fact that isomers containing energeticallydisfavored fragments can be formed in the supersonic expansion. Moreover, the OH···N structure is onlyobserved in the homochiral complex, which seems to indicate that the two enantiomers of the chromophoredo not select the same conformation of alaninol during the complexation process.
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