Mapping charged silver(i) adenine polymers, [Adx+ Agy−zH](y − z)+, via electrospray ionization tandem mass spectrometry experiments

Vrkic, Ana K.; Taverner, Thomas; O’Hair, Richard A. J.

doi:10.1039/b206824a

Cited by 25 publications

(31 citation statements)

References 64 publications

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“…However, the calculations clearly suggest that the formation of N-Ag-N bridges is favored and that the stabilization of the rare tautomer is a direct result of the metalation. These results are in agreement with previous findings predicted by DFT calculations, 35 and they are also in accordance with the experimentally observed proton shift to N7 due to metalation with platinum 58 and mercury. 59 The calculated silver ion affinity r E MP2 for the canonical tautomer with silver binding to N7 (a-9H-Ag7) is 51 kcal/mol, about 6 kcal/mol less stable than the global minimum tautomer a -1H-9H-Ag7.…”

Section: Adenine-ag + Complexessupporting

confidence: 95%

“…59 The calculated silver ion affinity r E MP2 for the canonical tautomer with silver binding to N7 (a-9H-Ag7) is 51 kcal/mol, about 6 kcal/mol less stable than the global minimum tautomer a -1H-9H-Ag7. Previous ion affinities estimated by Burda et al 30 and Vrkic et al 35 for the same complex amount to 37 kcal/mol and 40 kcal/mol, respectively. The small discrepancy between Vrkic et al …”

Section: Adenine-ag + Complexesmentioning

confidence: 97%

“…The relative ordering of the calculated stabilities is in good agreement with previous theoretical findings. [33][34][35] Accordingly, the abundance for finding the canonical tautomer c-1H is calculated as 3.8% compared to 72.8% and 23.0% for c-7H and c-7H , respectively.…”

Section: Isolated Adenine and Cytosine Monomersmentioning

confidence: 99%

“…Some adenine-Ag structures are investigated in ref. 35, while here all possible binding sites of all the different tautomeric forms of adenine and cytosine-the latter, up to our knowledge never studied-have been considered.…”

Section: Introductionmentioning

confidence: 99%

“…Previous ab initio studies have characterized nucleic acids and metal cations, [28][29][30][31][32][33][34][35][36][37] or alkali metals. 35,[38][39][40] However, structural data on metal DNA mispairs is scarce. 4 Only few structures have been suggested for the Ag c-a mispair, e.g.…”

Section: Introductionmentioning

confidence: 99%

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Structure and bonding of Ag(I)–DNA base complexes and Ag(I)–adenine–cytosine mispairs: An ab Initio study

Schreiber

González

2007

J Comput Chem

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High level ab initio calculations have been carried out to characterize the structure, bonding and energetics of Ag(I)-DNA base complexes, including adenine or cytosine, as well as Ag(I)-adenine-cytosine mispairs. The interactions of the Ag cation in all binding sites of all adenine and cytosine tautomers have been considered. The calculations show that in gas phase the canonical form of cytosine is stabilized upon metalation, whereas the lowest energy structure of Ag-adenine correspond to a rare tautomer. Interestingly, the theoretical inspection of metalated adenine-cytosine mispair reveals that the most stable structures are formed from the canonical cytosine and adenine tautomers. The lowest energy structure is planar with adenine and cytosine hydrogen-bonded. Within few kcal/mol nonplanar, conformationally very flexible structures are found, in which the Ag(I) crosslinks an endocyclic nitrogen of adenine and the oxygen of cytosine. Metalated reverse-Wobble type of structures, on the contrary, are predicted much higher in energy.

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Section: Adenine-ag + Complexessupporting

confidence: 95%

Section: Adenine-ag + Complexesmentioning

confidence: 97%

Section: Isolated Adenine and Cytosine Monomersmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Structure and bonding of Ag(I)–DNA base complexes and Ag(I)–adenine–cytosine mispairs: An ab Initio study

Schreiber

González

2007

J Comput Chem

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Gas‐Phase Synthesis of [Ag₄H]⁺ and Its Mediation of the CC Coupling of Allyl Bromide

Khairallah

O’Hair

2005

Angewandte Chemie

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The formation of carbon-carbon bonds mediated by metal surfaces and nanoparticles continues to attract considerable attention. [1, 2] Recent work on the interaction of allyl halides (C 3 H 5 X) with a range of metal surfaces revealed different reactivity that depends on both the metal as well as the halide. [3, 4] Of all the metal surfaces examined, silver surfaces appear to be the most effective at mediating carbon-carbon bond coupling of allyl halides to give 1,5-hexadiene. Two distinct pathways have been observed:[4a] 1) dissociative adsorption of C 3 H 5 X to give surface-bound allyl groups, which then undergo coupling, and 2) a coupling reaction between C 3 H 5 X and a surface-bound allyl group. Surface defects play a significant role in the selectivity of 1,5-hexadiene formation which increases from 20 % to greater than 60 % when chlorine atoms are preadsorbed on silver surfaces.[4b] Also of interest are the largely forgotten results of Tamura and Kochi, [5] who synthesized silver nanoparticles over 30 years ago and showed that they reacted with allyl bromide to give 1,5-hexadiene and silver bromide [Eq. (1)]. Here we describe the gas-phase assembly of the subvalent silver hydride cluster [Ag 4 H] + [6] and its subsequent ionmolecule reactions with allyl bromide.[Ag 4 H] + was "synthesized" in the gas phase by collisioninduced dissociation (CID) of a silver-amino acid precursor in a quadrupole ion trap (QIT) mass spectrometer.[7] The precursor was the silver ion cluster [(M + Ag-H) 3 + Ag] + (M = N,N-dimethylglycine), which was formed through electrospray ionization (ESI) of a mixture of silver nitrate (AgNO 3 ) and the amino acid.[ clusters (M = glycine or N,N-dimethylglycine). These reactions represent the first gas-phase assembly of silver clusters mediated by simple biomolecules. [9, 10] Interestingly, the anionic amino acid ligands act as the reductants; this is in contrast to the condensed-phase assembly of silver clusters and nanoparticles on biomolecular templates which requires the addition of reductants.[11]The ion-molecule reactions of these silver clusters with the allyl halides, CH 2 =CHCH 2 X (X = Cl, Br, and I) were examined. [12, 13] [Ag 4 H] + (m/z = 433) [14] exhibits the highest selectivity for CÀC bond coupling with allyl bromide, CH 2 = CHCH 2 Br (Figure 1 (m/z = 189) [14] in combination with the neutral cluster [Ag 3 Br 3 ][15] (Figure 1 c, Equation (4)). Overall, these equations combine to give a rare example of a metal-mediated CÀ C bond-coupling reaction [Eq. (5)] in the gas phase. [16] Additional CID studies and DFT (density functional theory) calculations [17] were carried out to gain further support that CÀC bond coupling had occurred. CID of [Ag(C 3

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The Controversial Orientation of Adenine on Gold and Silver

Harroun

2018

ChemPhysChem

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In which orientation does adenine adsorb on gold and silver surfaces? This question has been a matter of debate for over 30 years. Since the dawn of surface-enhanced Raman spectroscopy (SERS); it and other techniques such as tip-enhanced Raman spectroscopy (TERS), surface-enhanced infrared absorption spectroscopy (SEIRAS), scanning tunneling microscopy (STM), density functional theory (DFT) simulations, and more, have been used in many attempts to answer this seemingly straightforward, yet controversial, question. Herein, the timeline and recent advances on this topic are explored, and the frequently contradictory findings are put into context and discussed.

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Mapping charged silver(i) adenine polymers, [Adx+ Agy−zH](y − z)+, via electrospray ionization tandem mass spectrometry experiments

Cited by 25 publications

References 64 publications

Structure and bonding of Ag(I)–DNA base complexes and Ag(I)–adenine–cytosine mispairs: An ab Initio study

Structure and bonding of Ag(I)–DNA base complexes and Ag(I)–adenine–cytosine mispairs: An ab Initio study

Gas‐Phase Synthesis of [Ag₄H]⁺ and Its Mediation of the CC Coupling of Allyl Bromide

The Controversial Orientation of Adenine on Gold and Silver

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Mapping charged silver(i) adenine polymers, [Adx+ Agy−zH](y − z)+, via electrospray ionization tandem mass spectrometry experiments

Cited by 25 publications

References 64 publications

Structure and bonding of Ag(I)–DNA base complexes and Ag(I)–adenine–cytosine mispairs: An ab Initio study

Structure and bonding of Ag(I)–DNA base complexes and Ag(I)–adenine–cytosine mispairs: An ab Initio study

Gas‐Phase Synthesis of [Ag4H]+ and Its Mediation of the CC Coupling of Allyl Bromide

The Controversial Orientation of Adenine on Gold and Silver

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Gas‐Phase Synthesis of [Ag₄H]⁺ and Its Mediation of the CC Coupling of Allyl Bromide