Non-covalent interactions of the hydroperoxo group in crystalline adducts of organic hydroperoxides and their potassium salts

Abstract

The present study demonstrates the similarity of hydrogen bonding of hydroperoxo functionality in organic hydroperoxide crystalline adducts (HPCA) and the much larger group of crystalline peroxosolvates. Based on a systematic...

Dioxygen–halogen bonding exemplified by crystalline peroxosolvates of N,N′-bis(haloacetyl) bispidines

“…64 Moreover, the C-OH group forms H-bonds with H 2 O 2 molecules as a proton donor with lower energy (26 kJ mol À1 ), which is in agreement with the H 2 O 2 and H 2 O hydrogen bonding features in isomorphous peroxosolvates and hydrates. 53,64,91 The energies of XBs are lower than those of H 2 O 2 H-bonds (Table 2 and Tables S5-S7, ESI †). Specifically, the CH 2 -IÁ Á ÁO 2 H 2 XBs are characterized by energy values of 13 and 16 kJ mol À1 , exceeding the value for similar interaction in 3 (10 kJ mol À1 ).…”

“…62,63 The incorporation of the hydroperoxo group into an organic moiety and its cocrystallization with hydrogen peroxide could be a new option for accumulating a higher energy level in a crystalline material. While H-bonds play a structure-directing role in crystalline peroxosolvates of organic coformers 62,63 and adducts of organic hydroperoxides, 64 XBs, in particular Hal⋯O bonds, can also stabilize crystals, as has previously been shown for a number of energetic cocrystals. 10,65,66…”

“…94 The hydroperoxo fragment of hydrogen peroxide and an organic or inorganic hydroperoxide always acts as an H-bond donor, and hydrogen bonding of the hydroperoxo fragment leads to a decrease in the frequency of O-O stretching. 53,64 Indeed, the minimal reported value of the O-O stretching band (871 cm À1 ) in the FTIR spectra of crystalline peroxosolvates was found for urea peroxosolvate (NH 2 ) 2 CQOÁ H 2 O 2 , with six H-bonds formed by one H 2 O 2 molecule. 101 The O-O stretching band in the FTIR spectra of organic peroxides tends to appear in the range of 845-886 cm À1 .…”

Synergistic effect of hydrogen bonds and π-π interactions of B(C6F5)3·H2O/amides complex: Application in photoredox catalysis

“…There are four oxygen atoms and four hydrogen atoms, forming an eight-membered ring in the conformation of boat-chair via hydrogen bond possessing the lowest transannular strain and energy ( Figure 4 ). 51 , 52 The O … O distances in O–H … O hydrogen bond system range is 2.5627(15)−2.7583(15) Å, relatively shorter than the reported intermolecular O … O distances (2.70–3.00 Å), 53 , 54 suggesting the existence of stronger hydrogen bonds in crystal C1 .

Figure 4 Structure analysis of eight-membered rings of hydrogen bond Selected bond distances (Å): O1-H1 0.89(3), O1–H2 0.86(3), O3–H3 0.86(3), O3–H4 0.90 (3), O4 … H1 1.69(3), O2 … H2 1.97(3), O2 … H3 1.71(3), O4 … H4 1.83(3), O1 … O2 2.7583(15), O2 … O3 2.5627(15), O3 … O4 2.6578(15), O1 … O4 2.5659(15).

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Organoantimony Dihydroperoxides: Synthesis, Crystal Structures, and Hydrogen Bonding Networks

“…Previously, the similarities of hydrogen bonding between organic hydroperoxides and a large group of crystalline peroxosolvates were reported on the basis of the systematic analysis of the CSD. , It was found that the hydroperoxo group always participated in hydrogen bonding as a proton donor, and this type of hydrogen bonding played a predominant role in the crystal packing. To understand whether hydrogen bonding in antimony dihydroperoxides was governed by the same principles, we analyzed hydrogen bonding networks in the crystal structures of compounds I – VI .…”