Infrared spectra of protonated neurotransmitters: dopamine

dc.contributor.authorLagutschenkov, Anita
dc.contributor.authorLanger, Judith
dc.contributor.authorBerden, Giel
dc.contributor.authorOomens, Jos
dc.contributor.authorDopfer, Otto
dc.date.accessioned2016-07-01T06:27:31Z
dc.date.available2016-07-01T06:27:31Z
dc.date.issued2011
dc.descriptionDieser Beitrag ist mit Zustimmung des Rechteinhabers aufgrund einer (DFG geförderten) Allianz- bzw. Nationallizenz frei zugänglich.de
dc.descriptionThis publication is with permission of the rights owner freely accessible due to an Alliance licence and a national licence (funded by the DFG, German Research Foundation) respectively.en
dc.description.abstractThe infrared (IR) spectrum of the isolated protonated neurotransmitter dopamine was recorded in the fingerprint range (570–1880 cm−1) by means of IR multiple photon dissociation (IRMPD) spectroscopy. The spectrum was obtained in a Fourier transform ion cyclotron resonance mass spectrometer equipped with an electrospray ionization source, which was coupled to a free electron laser (FEL). The spectroscopic studies are complemented by quantum chemical calculations at the B3LYP and MP2 levels of theory using the cc-pVDZ basis set. Several low-energy isomers with protonation occurring at the amino group are predicted in the energy range 0–50 kJ mol−1. Good agreement between the measured IRMPD spectrum and the calculated linear absorption spectra is observed for the two gauche conformers lowest in energy (ΔE) and free energy (ΔG) at both levels of theory, denoted g−1 and g+1. Minor contributions of higher lying gauche isomers cannot be ruled out spectroscopically but their calculated energies suggest only minor population in the sampled ion cloud. In all these gauche structures, one of the three protons of the ammonium group is pointing toward the catechol subunit, thereby maximizing the intramolecular NH–π interaction of the positive charge with the aromatic ring. In total, 16 distinct vibrational bands are observed in the IRMPD spectrum and assigned to individual normal modes of the energetically most stable g−1 conformer, with deviations of less than 24 cm−1 (average 11 cm−1) between measured and calculated frequencies. Comparison with neutral dopamine reveals the effects of protonation on the geometric and electronic structure.en
dc.description.sponsorshipEC/FP7/226716/EU/European Light Sources Activities - Synchrotrons and Free Electron Lasers/ELISAen
dc.identifier.eissn1463-9084
dc.identifier.issn1463-9076
dc.identifier.pmid21152614
dc.identifier.urihttp://depositonce.tu-berlin.de/handle/11303/5747
dc.identifier.urihttp://dx.doi.org/10.14279/depositonce-5367
dc.language.isoen
dc.rights.urihttp://rightsstatements.org/vocab/InC/1.0/en
dc.subject.ddc540 Chemie und zugeordnete Wissenschaftende
dc.titleInfrared spectra of protonated neurotransmitters: dopamineen
dc.typeArticleen
dc.type.versionpublishedVersionen
dcterms.bibliographicCitation.doi10.1039/c0cp02133d
dcterms.bibliographicCitation.issue7
dcterms.bibliographicCitation.journaltitlePhysical chemistry, chemical physicsen
dcterms.bibliographicCitation.originalpublishernameRoyal Society of Chemistryde
dcterms.bibliographicCitation.originalpublisherplaceCambridgede
dcterms.bibliographicCitation.pageend2823
dcterms.bibliographicCitation.pagestart2815
dcterms.bibliographicCitation.volume13
tub.accessrights.dnbdomain
tub.affiliationFak. 2 Mathematik und Naturwissenschaften>Inst. Optik und Atomare Physikde
tub.affiliation.facultyFak. 2 Mathematik und Naturwissenschaftende
tub.affiliation.instituteInst. Optik und Atomare Physikde
tub.publisher.universityorinstitutionTechnische Universität Berlin
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