The specificity of the [NHN]+ hydrogen bonds in protonated naphthalene proton sponges

Sobczyk, L.

doi:10.1016/j.molstruc.2009.11.057

Cited by 17 publications

(18 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The computational findings for NHN + are in agreement with IR measurements reported for relative compounds by Sobczyk. 16 DMANH + is characterized by very low frequency ν(NHN) + stretching vibrations at ca. 500 cm −1 , which are consistent with the gas phase and solid-state CPMD results.…”

Section: Resultsmentioning

confidence: 99%

“Zwitterionic Proton Sponge” Hydrogen Bonding Investigations on the Basis of Car–Parrinello Molecular Dynamics

Jezierska

Panek

2015

J. Chem. Inf. Model.

View full text Add to dashboard Cite

1,8-Bis(dimethylamino)-4,5-dihydroxynaphthalene has been investigated on the basis of static DFT computations and Car-Parrinello molecular dynamics. The simulations were performed in the gas phase and in the solid state. The studied "zwitterionic proton sponge" possesses two, short intramolecular hydrogen bonds (O-H···O and N-H···N) classified as Low Barrier Hydrogen Bonds (LBHBs); therefore, the system studied is strongly anharmonic. In addition, the compound exists as a "zwitterion" in solution and in the solid state, thus the intramolecular hydrogen bonds belong to the class of charge-assisted interactions. The applied quantum-chemical methods enabled investigations of metric and spectroscopic parameters of the molecule. The time-evolution investigations of the H-bonding showed a strong delocalization of the bridge protons and their high mobility, reflected in the low barriers on the free energy surfaces. Frequent proton transfer phenomena were noticed. The power spectra of atomic velocity were computed to analyze the vibrational features associated with O-H and N-H stretching. A broad absorption was indicated for both hydrogen bridges. For the first time, Car-Parrinello molecular dynamics results are reported for the compound, and they indicate a broad, shallow but not barrierless, potential well for each of the bridge protons.

show abstract

Section: Resultsmentioning

confidence: 99%

“Zwitterionic Proton Sponge” Hydrogen Bonding Investigations on the Basis of Car–Parrinello Molecular Dynamics

Jezierska

Panek

2015

J. Chem. Inf. Model.

View full text Add to dashboard Cite

show abstract

“…The rigid scaffold chosen in this work to isolate the CIPB is based on the 1,8-disubstituted naphthalene derivatives shown in Scheme 1. These compounds are derivatives of 1·H + , the familiar "proton sponge" organic base (1,8-bis(dimethylamino)naphthalene), [12][13][14] and allow access to the N-H + -O and N-H + -F intramolecular Hbonding motifs (Scheme 1, 2·H + −4·H + ).…”

Section: Introductionmentioning

confidence: 99%

Origin of the diffuse vibrational signature of a cyclic intramolecular proton bond: Anharmonic analysis of protonated 1,8-disubstituted naphthalene ions

DeBlase

Bloom

Lectka

et al. 2013

The Journal of Chemical Physics

View full text Add to dashboard Cite

We analyze the structures and spectral signatures of the cyclic intramolecular proton bond, N-H(+)-A, A = O and F, formed when an excess proton is added to derivatives of the 1,8-disubstituted naphthalene scaffold. These compounds provide a quasi-rigid framework with which to study the spectral complexity often associated with the N-H(+)-A entity. Vibrational spectra were obtained by monitoring photodissociation of weakly bound H2 adducts of the mass-selected ions cooled close to 10 K. Several bands across the 900-3500 cm(-1) spectral range were traced to involvement of the bridging proton by their telltale shifts upon selective H∕D isotopic substitution at that position. We account for the complex patterns that occur near the expected locations of the NH stretching fundamentals in the context of background levels mixing with a "bright" zero-order state through cubic terms in the potential energy expansion. Thus, this system provides a detailed picture of one of the mechanisms behind the line broadening often displayed by embedded excess protons. It does so in a sufficiently sparse density of states regime that many discrete transitions are observed in the vicinity of the harmonic stretching transition involving displacement of the trapped proton.

show abstract

“…16,17 In these complexes, DMAN typically extracts a proton from the organic acid inducing the formation of O-H⋯O − charge-assisted hydrogen bonds (CAHBs) between acid molecules. 11,15,16,18 The extracted proton is held by the DMAN molecule in an asymmetric [19][20][21][22] intramolecular [N-H⋯N] + hydrogen bond (IHB). 11 The association of the DMAN : acid components in the crystal packing consistently occurs via weak HB interactions in an assembly where the hydrogen bonded acid (ACID − ) unit is oriented towards the DMAN cation methyl groups and IHB (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Tuning charge-assisted and weak hydrogen bonds in molecular complexes of the proton sponge DMAN by acid co-former substitution

et al. 2018

View full text Add to dashboard Cite

show abstract

The specificity of the [NHN]+ hydrogen bonds in protonated naphthalene proton sponges

Cited by 17 publications

References 27 publications

“Zwitterionic Proton Sponge” Hydrogen Bonding Investigations on the Basis of Car–Parrinello Molecular Dynamics

“Zwitterionic Proton Sponge” Hydrogen Bonding Investigations on the Basis of Car–Parrinello Molecular Dynamics

Origin of the diffuse vibrational signature of a cyclic intramolecular proton bond: Anharmonic analysis of protonated 1,8-disubstituted naphthalene ions

Tuning charge-assisted and weak hydrogen bonds in molecular complexes of the proton sponge DMAN by acid co-former substitution

Contact Info

Product

Resources

About