Halogen bonding organocatalysis enhanced through intramolecular hydrogen bonds

Riel, Asia Marie S.; Decato, Daniel A.; Sun, Jiyu; Berryman, Orion B.

doi:10.1039/d1cc05475a

Cited by 24 publications

(29 citation statements)

References 46 publications

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“…21 A hydrogen bond to the electronegative belt of a halogen bond donor further polarizes and strengthens the halogen bond donor. HBeXBs have influenced macromolecule stability, 22 small molecule anion binding, 23 organocatalysis, 24,25 and have been quantified in a fundamental solution study. 16 Each of these studies employ "traditional" -OH or -NH donors, prompting us to consider the efficacy of C-H hydrogen bond donors to operate in a similar manner.…”

Section: Introductionmentioning

confidence: 99%

Pushing the limits of the hydrogen bond enhanced halogen bond—the case of the C–H hydrogen bond

Decato¹,

Sun

Boller

et al. 2022

Chem. Sci.

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Section: Introductionmentioning

confidence: 99%

Pushing the limits of the hydrogen bond enhanced halogen bond—the case of the C–H hydrogen bond

Decato¹,

Sun

Boller

et al. 2022

Chem. Sci.

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“…There is a certain amount of both experimental and computational support for the central idea that activity of a halogen atom as a proton acceptor in one or more HBs will accentuate its XB potency. , The replacement of Tyr within a protein by m -chlorotyrosine raised its stability as well as its enzymatic activity as the newly introduced Cl atom engaged in a XB with the carbonyl O of a neighboring Gly. This XB was facilitated by the HB formed by this Cl to the OH on the tyrosine ring, even if the geometry of this internal bond was not in its optimal geometry.…”

Section: Discussionmentioning

confidence: 99%

“…Experimental and theoretical data ,− indicate just such a concept, albeit within the specialized framework of cation–anion interactions involved in halide binding. This HB/XB cooperativity has demonstrated implications for protein structure and function , and catalysis. , …”

Section: Introductionmentioning

confidence: 99%

“…This HB/XB cooperativity has demonstrated implications for protein structure and function 51,52 and catalysis. 53,54 There are a number of important questions whose answers carry potentially far-reaching implications. In the first place, just how much of a strengthening effect on a halogen bond can be expected from one or more HBs to the X atom?…”

Section: ■ Introductionmentioning

confidence: 99%

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Ability of Peripheral H Bonds to Strengthen a Halogen Bond

Scheiner

2022

J. Phys. Chem. A

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Quantum calculations study the manner in which the involvement of a halogen atom as a proton acceptor in one or more H bonds (HBs) affects the strength of the halogen bond (XB) it can form with a nucleophile aligned with the X σ-hole. A variety of Lewis acids wherein X = F, Cl, Br, and I are attached to a tetrel atom C or Ge engaged in a XB with nucleophile NH3. One, two, and three HF molecules were positioned perpendicular to the XB axis so that they could form a HB to the X atom. Each such HB strengthened the XB by an increment of 1 kcal/mol or more that does not attenuate as each new HB is added, potentially increasing the interaction energy manyfold. Additionally, the presence of one or more HBs facilitates the formation of a XB by molecules which are reluctant to engage in such a bond in the absence of these auxiliary interactions. Even the F atom, which avoids such a XB, can be coaxed to participate in a XB of moderate strength by one or more of these external HBs.

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“…The number of investigations concerning halogen bonding can be compared with the solar‐cells “big boom”. A lot of recent research data can be easily found in the literature [13–18] . In Russia such studies are actively being developed by the leading research groups of Prof. V. Yu.…”

Section: Introductionmentioning

confidence: 99%

Halogen Bonding Channels for Magnetic Exchange in Cu(II) Complexes with 2,5‐Di(methylthio)‐1,3,4‐thiadiazole

Лавренова

Ivanova

Glinskaya

et al. 2023

Chemistry An Asian Journal

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Copper(II) complexes with 2,5-bis(methylthio)-1,3,4thiadiazole (tda) formulated as [Cu(tda) n X 2 ] (n = 2, X = Cl À , Br À , C 2 N 3 À ; n = 1, X = C 2 N 3 À ) have been isolated and fully characterized. The crystal structures of all compounds have been determined using single-crystal X-ray diffraction (SCXRD). A study of the magnetic susceptibility in the range 1.77-300 K has shown that magnetic properties of the [Cu(tda) 2 Cl 2 ] and [Cu(tda) 2 Br 2 ] complexes match those of 1D chains of antiferromagnetically-coupled Cu 2 + ions. The intrachain interaction J in [Cu(tda) 2 Cl 2 ] turns out to be ~1.2 times weaker than in its bromide analogue. In its turn, [Cu-(tda) 2 (C 2 N 3 ) 2 ] exhibits J being an order of magnitude smaller and of the opposite ferromagnetic sign. Halogen bonding (HB) between adjacent complexes is much stronger than the H-bonds or π-π interactions between tda ligands according to the DFT calculations.

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Halogen bonding organocatalysis enhanced through intramolecular hydrogen bonds

Abstract: Recent results indicate a halogen bond donor is strengthened through direct interaction with a hydrogen bond to the electron-rich belt of the halogen. Here, this Hydrogen Bond enhanced Halogen Bond...

Cited by 24 publications

References 46 publications

Pushing the limits of the hydrogen bond enhanced halogen bond—the case of the C–H hydrogen bond

Pushing the limits of the hydrogen bond enhanced halogen bond—the case of the C–H hydrogen bond

Ability of Peripheral H Bonds to Strengthen a Halogen Bond

Halogen Bonding Channels for Magnetic Exchange in Cu(II) Complexes with 2,5‐Di(methylthio)‐1,3,4‐thiadiazole

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