Tautomerism and electronic spectroscopy of protonated 1- and 2-aminonaphthalene

NOBLE, JENNIFER A.; BROQUIER, MICHEL; GRÉGOIRE, GILLES; SOORKIA, SATCHIN; PINO, GUSTAVO; MARCECA, ERNESTO; DEDONDER-LARDEUX, CLAUDE; JOUVET, CHRISTOPHE

PHYSICAL CHEMISTRY CHEMICAL PHYSICS

ROYAL SOC CHEMISTRY

Año: 2018 vol. 20 p. 6134 - 6145

1463-9076

Experimental and theoretical investigations of the excited states of protonated 1- and 2-aminonaphthalene  are presented. The electronic spectra are obtained by laser induced photofragmentation of the ions captured in a cold ion trap. Using ab initio calculations, the electronic spectra can be assigned to different tautomers which have the proton on the amino group or on the naphthalene moiety. It is shown that the tautomer distribution can be varied by changing the electrospray source conditions, favoring either the most stable form in solution (amino protonation) or that in the gas phase (aromatic ring protonation). Calculations for larger amino-polyaromatics predict that these systems should behave as ??proton sponges?? i.e. have a proton affinity larger than 11 eV.