Nitrogen is equally electronegative as chlorine but also more compact.Whether you consider hydrogen bonding as purely electrostatic or having a covalent character (The lone pair on atom X overlaps the molecular orbital in the H-Y bond of an adjacent molecule, thus partially delocalizing the bond), the more compact structure of nitrogen offers an advantage.

Sep 10, 2012 · That's a covalent bond between hydrogen and chlorine, not a hydrogen bond. Hydrogen bonds are a form of weak noncovalent bonding acting between molecules that contain O-H, N-H and F-H groups where the hydrogen is partially ionized. Now whether chlorine participates in hydrogen bonding is something I don't know but I'll personally say "no".

Oct 26, 2020 · $\begingroup$ A hydrogen bond by definition needs three centers to be formed: the donor atom(Dn), the hydrogen itself (H) and an acceptor atom (Ac) to form a setup like Dn–H···Ac .A bond between H and Cl has only two centres: the hydrogen(H) and chlorine(Cl).

Jun 20, 2018 · In reality, the strongest hydrogen bonds involve nitrogen, oxygen, or fluorine, but most nonmetals can form such bonds if they have an electron pair to donate to the bond. Hydrogen bonding with chlorine is seen in the $\ce{HCl_2^-}$ [1], which is analogous to the more familiar bifluoride ion, as well as chlorine-bearing organic compounds[2 ...

May 17, 2015 · Seeing that both oxygen and chlorine have a small difference in their electronegativity (oxygen being roughly 3.5 and chlorine being roughly 3.0), why does chlorine in a hydrogen chloride molecule ($\ce{HCl}$) have a dipole-dipole interaction, while the oxygen in a water molecule ($\ce{H2O}$) causes the water molecule to have a stronger form of ...

May 25, 2019 · To get the strongest hydrogen bonds you need a compact atom to concentrate the negative charge for electrostatic attraction and to overlap well with the hydrogen 1s orbital for the molecular orbital/delocalized covalent bond contribution (yes, the latter is a thing.) Nitrogen has that, chlorine not so much.

Aug 29, 2018 · Hydrogen bonds to chlorine atoms are known. In the gas phase HCl dimers are hydrogen bonded but the bond has only about half the dissociation energy of $\ce{(HF)2}$ which has a larger electrostatic attraction energy. The adduct $\ce{HCl\cdots OH2}$ is also known and has a similar hydrogen bond energy to that of $\ce{HOH\cdots OH2}$.

Dec 16, 2008 · Although one might expect hydrogen bonding to occur between HCl molecules, since Cl's electronegatively is on par with nitrogen for instance. However, chlorine is too large, and thus the lone pairs are too diffuse ie. not concentrated enough, and hence hydrogen bond attractions between Cl's lone pairs and hydrogen atoms can not form.

Oct 20, 2016 · $\begingroup$ The existence of hydrogen bonds involving chlorine atoms was disputed a while ago, but experimental data show that chlorine atoms can form hydrogen bonds, and are in fact very common. See C.B. Aakeröy et al., The C–H···Cl hydrogen bond: does it exist? New J. Chem., 1999,23, 145-152. DOI: 10.1039/A809309A $\endgroup$ –

Apr 29, 2015 · My notes states that fluorine is too highly electronegative and hence clings on too tightly to its lone pair of electrons and so it cannot accept hydrogen bonds as well. However, it also stated that a hydrogen bond will be stronger if the electron density on the electron rich atom the stronger the hydrogen bond.