Enthalpy and entropy contributions to the equilibrium of the hydrogen bonding interaction between 1-octylthymine and 9-octyladenine

Salas, Magali; Gordillo, Barbara; González, Felipe J.

doi:10.3998/ark.5550190.0004.b09

Cited by 10 publications

(3 citation statements)

References 12 publications

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“…28 Although the K Thy-DAT could not be measured in toluene-d 8 by NMR titration, temperature-dependent NMR measurements of solutions of Thy-PPO-2200-Thy 6b, DAT-PPO-2200-DAT 7b, and Thy-PPO-2200-DAT 5b allowed the estimation of K Thy-DAT , as well as K Thy-Thy and K DAT-DAT , as a function of temperature (Table 2) (see ESI † for detailed procedure and equations). 35 If values of dimerisation constants K Thy-Thy and K DAT-DAT are close to those recently reported by Binder 36 (70 AE 14 L mol À1 and 22 AE 7 L mol À1 resp. at 27 C), the value of the association constant K Thy-DAT was 10 times higher (2.6 AE 1.3 Â 10 3 L mol À1 ).…”

Section: Association Constant In Dmso Chloroform and Toluenesupporting

confidence: 90%

Binding and supramolecular organization of homo- and heterotelechelic oligomers in solutions

2014

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Section: Association Constant In Dmso Chloroform and Toluenesupporting

confidence: 90%

Binding and supramolecular organization of homo- and heterotelechelic oligomers in solutions

2014

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“…2). 43 In this particular case an infinite 2D layer of hydrogen bonded nucleobases is not formed because the octyl chain of the adenine is arranged at the opposite side with respect to the octyl chain of the thymine.…”

Section: Introductionmentioning

confidence: 99%

Experimental and theoretical study of uracil derivatives: the crucial role of weak fluorine–fluorine noncovalent interactions

et al. 2010

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We have recently communicated the important role of lone pair-p, p-p and hydrophobic interactions in the solid architecture of 5-fluoro-1-hexyluracil and 1-hexyluracil (CrystEngComm, 2010, 12, 362-365). As a matter of fact, the simple substitution of a hydrogen atom by a fluorine atom has an enormous consequence in the solid state structure. It has been demonstrated that this is due to an increase in the p-acidity of the ring. In this article we extend the study to other uracil derivatives, where we have changed the hydrophobicity of the hexyl chain by introducing hydrophilic groups in the substituent, such as hydroxyl or carboxylic groups. The latter compounds, i.e. (N 1 -(3-hydroxypropyl)-5-fluorouracil and N 1 -(4-hydroxycarbonylbutyl)-5-fluorouracil monohydrate present interesting fluorine-fluorine interactions that are very important in determining the crystal packing.

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“…These different values of K are in agreement with those obtained in the same experimental conditions for adenine and thymine alone. 32,33 In our case, the presence of cyclodextrin does not affect the interactions between nucleobases (AA, TT, or AT) in CDCl 3 .…”

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Potential Supramolecular Cyclodextrin Dimers Using Nucleobase Pairs

Hamon¹,

Violeau²,

Turpin³

et al. 2009

Synlett

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The synthesis of six new cyclodextrin derivatives having nucleobase moiety is described. These two moieties are linked by different spacers, such as aminoethyl and 1,2,3-triazolyl groups. Example of association constants for complexation of adenine and thymine derivatives: K AT = 385 M -1 using NMR methodology is reported. Study of interaction between four cyclodextrin derivatives and one adamantyl guest is described by ITC.Cyclodextrins (CD) are a family of cyclic oligosaccharides composed of a-(1→4)-linked D-glucopyranose units in 4 C 1 chair conformation. The most common CD have six, seven, and eight glucopyranose units and are referred to as a-, b-, and g-CD, respectively. As a consequence of the structure, the molecule is hydrophilic and features a conical cavity that is essentially hydrophobic in nature. This property enables them to be successfully used as drug carrier, 1-3 separation reagents, 4-6 enzyme mimics, 7,8 photochemical sensors, 9,10 catalysis, 11,12 host-guest interactions, 13 and molecular recognition. 14 In comparison with CD monomers, CD dimers tethered by a spacer of different sizes and shapes have two hydrophobic cavities in a close vicinity. 15 This property may afford distinctly different apparent association abilities and molecular selectivities. 16 Various structural architectures of covalent CD dimers could be prepared but one challenge will be to obtain supramolecular CD dimers with noncovalent interactions such as H bonding, staking, electrostatic, and charge-transfer interactions. The equilibrium between the noncovalent dimers and the corresponding monomers could permit to modulate the association. Unexpectedly, these molecular organization behaviors have not been extensively investigated. The supramolecular assembly could be obtained by association of nucleobases such as adenine and thymine or guanine and cytosine. Few examples of CD derivative having nucleobase were described in the literature but only the study of CD monomers were reported. [17][18][19][20][21] In this paper, we reported our preliminary work regarding the synthesis of different CD monomers having a nucleobase such as adenine and thymine and their potential application for the formation of supramolecular CD dimers. The target compounds 8, 9, 11, and 12 had three major structural variations and were novel CD derivatives. First modulation was the glycone moiety: amino-b-CD, azido-b-CD, or amino-permethylated b-CD derivatives. Second variation was the nature of the linker: aminoethyl group or 1,2,3-triazol-4-ylmethyl group. Third modulation was the nucleobase: adenine or thymine.N-Alkylation of pyrimidine bases gave predominantly N1-monosubstituted and N1,N3-bis-substituted derivatives. In order to prepare regioselectively the N1-alkylated pyrimidine, silylation of the nucleobase was developed. Coupling of dibromoethane with silylated thymine (1) in presence of NaI at 105°C without solvent furnished the bromide 2 22-25 in 32% yield. Coupling of propargyl bromide with silylated thymine at 80°C in acetonitrile gave t...

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Enthalpy and entropy contributions to the equilibrium of the hydrogen bonding interaction between 1-octylthymine and 9-octyladenine

Cited by 10 publications

References 12 publications

Binding and supramolecular organization of homo- and heterotelechelic oligomers in solutions

Binding and supramolecular organization of homo- and heterotelechelic oligomers in solutions

Experimental and theoretical study of uracil derivatives: the crucial role of weak fluorine–fluorine noncovalent interactions

Potential Supramolecular Cyclodextrin Dimers Using Nucleobase Pairs

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