DABCO mono-betaine hydrate studied by X-ray diffraction, DFT calculations and spectroscopic methods

Barczyński, P.; Dega‐Szafran, Z.; Katrusiak, Andrzej; Perdoch, Waldemar; Szafran, M.

doi:10.1016/j.molstruc.2009.05.050

Cited by 14 publications

(9 citation statements)

References 25 publications

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“…However in the DABCO compounds at high temperature the diaminoethylene bridges were planar, while the propeller conformation was assumed at low temperatures. A similar planar conformation was observed in the DABCO-mono-betaine, in which the atoms are located on the mirror plane [36].…”

Section: Resultssupporting

confidence: 70%

“…[36]. DABCO mono-betaine was dissolved in the excess of 30% hydrochloric acid, and the solution was evaporated to dryness under the reduced pressure.…”

Section: Methodsmentioning

confidence: 99%

“…Similarly as 1,4-dimethylpiperazine [18], 1,4-diazabicyclo[2.2.2]octane (DABCO) forms two betaines: DABCO mono-betaine [36] and DABCO di-betaine [34]. 1,4-Dimethylpiperazine mono-betaine (MBPZ) has two non-equivalent proton-acceptor centers and forms a crystalline complex with two molecules of HCl or HBr, while 1,4-dimethylpiperazine di-betaine (DBPZ) has two equivalent proton-acceptor centers and forms the complex with one molecule of HCl.…”

Section: Introductionmentioning

confidence: 99%

“…Recently we have described the synthesis and structure of DABCO mono-betaine [36], and in this report we extent our investigation of synthesis and characterization of DABCO mono-betaine hydrochloride by X-ray diffraction, FTIR spectroscopy, and DFT calculations to provide more information on the hydrogen bonds and other interatomic interactions. The pK a of DABCO, DABCO monoand di-betaines are determined by the potentiometric titration of their hydrohalides.…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Unusual 2:3:2 complex of DABCO mono-betaine with HCl and H2O studied by X-ray diffraction, DFT calculations and spectroscopic methods

Barczyński¹,

Dega‐Szafran²,

Katrusiak³

et al. 2009

Journal of Molecular Structure

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Section: Resultssupporting

confidence: 70%

“…[36]. DABCO mono-betaine was dissolved in the excess of 30% hydrochloric acid, and the solution was evaporated to dryness under the reduced pressure.…”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Unusual 2:3:2 complex of DABCO mono-betaine with HCl and H2O studied by X-ray diffraction, DFT calculations and spectroscopic methods

Barczyński¹,

Dega‐Szafran²,

Katrusiak³

et al. 2009

Journal of Molecular Structure

Self Cite

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“…For N ‐DMP, N ‐DABCO, N ‐MPY, and N ‐TMA, this band can be assigned to the symmetric stretch of OSO in the SO 2 N + R 3 pendent group 56. This band may also be associated with ring vibrations, such as deformation and CH 2 twist of the cyclic pendent groups in N ‐DMP,61,62 N ‐DABCO,63 and N ‐MPY 64. This band shifts to lower wave numbers, 1016–1017 cm −1 , in the phosphonium cation AEM, N ‐TMP and is associated with the symmetric stretch of OSO in the SO 2 P + R 3 pendent group.…”

Section: Resultsmentioning

confidence: 99%

Anion exchange membranes derived from nafion precursor for the alkaline fuel cell: Effect of cation type on properties

Salerno

Elabd

2012

J of Applied Polymer Sci

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Highly stable hydroxide conducting membranes are necessary for solid-state alkaline fuel cells to have long performance lifetimes. In this study, we used solid-state chemistry to synthesize Nafion-based anion exchange membranes (AEMs) with a variety of covalently attached cations, including trimethylammonium, trimethylphosphonium, piperazinium, pyrrolidinium, pyridinium, and quaternized 1,4-diazabicyclo[2.2.2]octane. Infrared spectroscopy confirms a partial asymmetric functionalization of all cations with the exception of pyridinium. The AEMs that were successfully synthesized all exhibited sufficient water uptake and conductivity. The effect of cation type on AEM chemical and thermal stability was investigated as a function of various conditions (e.g., hydration levels, temperature, and pH). High chemical and thermal stability was observed for all successfully synthesized AEMs with the exception of the trimethylphosphonium cation AEM.

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Critical test of some computational methods for prediction of NMR 1H and 13C chemical shifts

Toomsalu

Burk

2015

J Mol Model

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Performance of 18 DFT functionals (B1B95, B3LYP, B3PW91, B97D, BHandHLYP, BMK, CAM-B3LYP, HSEh1PBE, M06-L, mPW1PW91, O3LYP, OLYP, OPBE, PBE1PBE, tHCTHhyb, TPSSh, wB97xD, VSXC) in combinations with six basis sets (cc-pVDZ, aug-cc-pVDZ, cc-pVTZ, aug-cc-pVTZ, IGLO-II, and IGLO-III) and three methods for calculating magnetic shieldings (GIAO, CSGT, IGAIM) was tested for predicting (1)H and (13)C chemical shifts for 25 organic compounds, for altogether 86 H and 88 C atoms. Proton shifts varied between 1.03 ppm to 12.00 ppm and carbon shifts between 7.87 ppm to 209.28 ppm. It was found that the best method for calculating (13)C shifts is PBE1PBE/aug-cc-pVDZ with CSGT or IGAIM approaches (mae = 1.66 ppm), for (1)H the best results were obtained with HSEh1PBE, mPW1PW91, PBE1PBE, CAM-B3LYP, and B3PW91 functionals with cc-pVTZ basis set and with CSGT or IGAIM approaches (mae = 0.28 ppm). We found that often larger basis sets do not give better results for chemical shifts. The best basis sets for calculating (1)H and (13)C chemical shifts were cc-pVTZ and aug-cc-pVDZ, respectively. CSGT and IGAIM NMR approaches can perform really well and are in most cases better than popular GIAO approach.

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DABCO mono-betaine hydrate studied by X-ray diffraction, DFT calculations and spectroscopic methods

Cited by 14 publications

References 25 publications

Unusual 2:3:2 complex of DABCO mono-betaine with HCl and H2O studied by X-ray diffraction, DFT calculations and spectroscopic methods

Unusual 2:3:2 complex of DABCO mono-betaine with HCl and H2O studied by X-ray diffraction, DFT calculations and spectroscopic methods

Anion exchange membranes derived from nafion precursor for the alkaline fuel cell: Effect of cation type on properties

Critical test of some computational methods for prediction of NMR 1H and 13C chemical shifts

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