Thermodynamic parameters for hydrogen bonding of chloroform with Lewis bases in cyclohexane. Proton magnetic resonance study

Wiley, Gary R.; Miller, Sidney I.

doi:10.1021/ja00765a001

Cited by 65 publications

(21 citation statements)

References 2 publications

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“…A similar behaviour was observed for several thieno [3,2-b]pyridine derivatives synthesized in our lab [22][23][24]. The formation of hydrogen bonds between chloroform and these proton acceptor quinoline derivatives can also explain the lower fluorescence quantum yield values in this solvent [25,26].…”

Section: Fluorescence Studies In Several Solventssupporting

confidence: 81%

Benzothienoquinolines: New one-pot synthesis and fluorescence studies of their interaction with DNA and polynucleotides

Rodrigues

Carvalho

Cardoso

et al. 2014

Journal of Photochemistry and Photobiology A: Chemistry

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a b s t r a c tIn this work, we were able to obtain the benzothieno[3,2-b]quinoline 1 and benzothieno[2,3-c]quinoline 2 using a new one-pot procedure from the reaction of the commercially available 3-bromobenzo[b]thiophene-2-carbaldehyde with 2-aminophenylpinacolborane under Suzuki coupling conditions using a stereochemically hindered ligand, 2-(cyclohexylphosphane)biphenyl and Ba(OH) 2 ·8H 2 O as the base.Fluorescence properties of the benzothieno[3,2-b]quinoline 1 and the benzothieno[2,3-c]quinoline 2 were studied in solvents of different polarity. Both compounds exhibit a solvent sensitive emission, compound 1 being less fluorescent (˚F < 0.05) than compound 2 (0.04 ≤ ˚F ≤ 0.10).The interaction of these compounds with salmon sperm DNA and synthetic double-stranded heteropolynucleotides, poly(dA-dT)·(dA-dT) and poly(dG-dC)·(dG-dC), was studied using spectroscopic methods, allowing the determination of the intrinsic binding constants and binding site sizes. The interaction of both compounds is stronger with adenine-thymine (A-T) base pairs. Compound 1 is the most intercalative in salmon sperm DNA (47%) and polynucleotides (46-49% of intercalated molecules), while for compound 2, 41% is intercalated in salmon sperm DNA and only 8% in poly(dG-dC)·(dG-dC). Docking studies indicate that compound 1 interacts more strongly with DNA than compound 2, with a significant value of binding free energy in the case of intercalation. Minor groove binding is also very favourable and, probably, both mechanisms occur with a preponderance of intercalation in the case of compound 1.Overall, these results indicate that both benzothienoquinolines interact with nucleic acids by both intercalation and groove binding.

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Section: Fluorescence Studies In Several Solventssupporting

confidence: 81%

Benzothienoquinolines: New one-pot synthesis and fluorescence studies of their interaction with DNA and polynucleotides

Rodrigues

Carvalho

Cardoso

et al. 2014

Journal of Photochemistry and Photobiology A: Chemistry

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“…The error limits, indicated by the broken lines (4 to 12 %), show that not much is to be gained by extending the measurements into the region of low B,, even if this were feasible. Although the use of an exact expression in place of equation (5) might perhaps allow for small increases in the range of s, 15 it should be apparent that one will have to be satisfied with even smaller s limits and correspondingly larger uncertainties in K , if weaker 1 :I complexes are to be investigated.…”

Section: Ak/k > As(s-* + (1 -S ) -~)~/~mentioning

confidence: 99%

“…The serious problem here is that weak associations with small and uncertain 1AH"J values magnify the problems of fitting or using equation (10). 15 We now take up several problems which bear on structural effects in process (1). Using binary mixtures of acid and base, some workers have judged the strength of a hydrogen bond by the magnitude of (6, -dA(B))?'…”

Section: Structural Effects On Donor-thiol Associationmentioning

confidence: 99%

Thermodynamic data for hydrogen bonding of thiols with Lewis bases in carbon tetrachloride. Weak association by the PMR method

Goldberg

Miller

1972

Org. Magn. Reson.

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Data for 30 hydrogen bonding pairs taken from the alkanethiols, i‐C3H7SH, nC3H9SH and t‐C4H9SH, and 16 bases have been obtained by a PMR method. Representative data for i‐C3H7SH at 304 ± 2°K are (base, 102K in M−1, –ΔH° in kcal/mole): (CH2)4S, 3·1, 0·8; (CH3)2S, 3·0, 0·9; (CH3)2S2, 3·7, 0·5; (CH3)2CO, 4·7, 0·9; CH3COOC2H5, 5·7, 1·1; (CH2)4O, 6·1, 1·0; HCON(CH3)2, 12, 0·9; (CH3 O)2 SO, 12, 0·9; (C2 H5O)3PO, 6·5, 1·0; CH3 (CH3 O)2PO, 18, 1·0; ((CH3)2N)2 CO, 5·9, 1·1; CH3 CN, 13, 0·6. In essence, the problems and errors involved in obtaining equilibrium data for weak complexes stem from the limited concentration rangethat is accessible. This leads to large uncertainties in the quantities K, ΔH° and ΔS°. Structural effects on hydrogen bonding at the sulfur site, both as Lewis acid or base, are discussed. Two erroneous PMR methods in the literature used for assessing the strength of hydrogen bonds are pointed out.

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“…The determination of adduct stoichiometry, together with the equilibrium, or formation, constant has been the subject of some attention in the past (5)(6)(7)(8)(9), with many authors putting undue confidence on unreliable data (6)(7)(8). The important work of Person (5) emphasized that the most reliable values for the formation constant are obtained when the concentration of the adduct (or complex) is approximately the same as that of the unbound concentration of the most dilute component.…”

Section: Introductionmentioning

confidence: 99%

Determination of the Stoichiometry of the Adducts Formed between some Heterocyclic Bases and Copper(II) Bis(diethyldithiocarbamate) in Various Solvents

Farmer¹,

Herring²,

Tapping³

1973

Can. J. Chem.

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Thermodynamic parameters for hydrogen bonding of chloroform with Lewis bases in cyclohexane. Proton magnetic resonance study

Cited by 65 publications

References 2 publications

Benzothienoquinolines: New one-pot synthesis and fluorescence studies of their interaction with DNA and polynucleotides

Benzothienoquinolines: New one-pot synthesis and fluorescence studies of their interaction with DNA and polynucleotides

Thermodynamic data for hydrogen bonding of thiols with Lewis bases in carbon tetrachloride. Weak association by the PMR method

Determination of the Stoichiometry of the Adducts Formed between some Heterocyclic Bases and Copper(II) Bis(diethyldithiocarbamate) in Various Solvents

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