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What type of intermolecular forces will dominate Diethyl ether?
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Lizzy Due?as Gaytan
What type of intermolecular forces will dominate Diethyl ether?
As you have already figured out, diethyl ether is a small dipole due to the electronegativity difference between carbon and oxygen, which can also be seen in this electron density plot. As both dipole moment vectors point roughly in the same direction, they do not cancel each other out like in the case of carbon dioxide, so the molecule has a net dipole moment and is therefore (weakly) polar.
London dispersion forces, which result from short-lived dipoles induced by fluctuations in the electron shell of molecules, are also present. They are responsible for the weak interactions between the alkyl chains, like in other alkanes and non-polar molecules. The permanent dipoles can also interact with each other, in the form of intermolecular attractive interactions between centers with $\delta+$ and $\delta-$ partial charge (and likewise repulsion between centers of equal partial charge).
Hydrogen bonding between C-H groups and oxygens, although possible in principle (see comments to your question) and, for example, found in protein structures, can be neglected in this case due to the low number of donors and the weakness of the interaction (< 17 kJ/mol). Nevertheless, the ether oxygen can act as a hydrogen bond acceptor in combination with better hydrogen bond donors like OH groups, which explains why diethyl ether is sparingly soluble in water despite its low polarity (69 g/l at 20 °C (source)). On the other hand, the absence of hydrogen bonding between ether molecules becomes apparent in the much lower boiling point of diethyl ether (34.6 °C, source) compared to water.
As you have already figured out, diethyl ether is a small dipole due to the electronegativity difference between carbon and oxygen, which can also be seen in this electron density plot. As both dipole moment vectors point roughly in the same direction, they do not cancel each other out like in the case of carbon dioxide, so the molecule has a net dipole moment and is therefore (weakly) polar.
London dispersion forces, which result from short-lived dipoles induced by fluctuations in the electron shell of molecules, are also present. They are responsible for the weak interactions between the alkyl chains, like in other alkanes and non-polar molecules. The permanent dipoles can also interact with each other, in the form of intermolecular attractive interactions between centers with $\delta+$ and $\delta-$ partial charge (and likewise repulsion between centers of equal partial charge).
Hydrogen bonding between C-H groups and oxygens, although possible in principle (see comments to your question) and, for example, found in protein structures, can be neglected in this case due to the low number of donors and the weakness of the interaction (< 17 kJ/mol). Nevertheless, the ether oxygen can act as a hydrogen bond acceptor in combination with better hydrogen bond donors like OH groups, which explains why diethyl ether is sparingly soluble in water despite its low polarity (69 g/l at 20 °C (source)). On the other hand, the absence of hydrogen bonding between ether molecules becomes apparent in the much lower boiling point of diethyl ether (34.6 °C, source) compared to water.
Clarifying a portion of the answer in the "Best Answer" you cannot have hydrogen bonding with a C-H bond. You only have hydrogen bonding with F-H, O-H, and N-H bonds. The hydrogen bonding in proteins usually results from amide hydrogen bonding shown in the image below
Clarifying a portion of the answer in the "Best Answer" you cannot have hydrogen bonding with a C-H bond. You only have hydrogen bonding with F-H, O-H, and N-H bonds. The hydrogen bonding in proteins usually results from amide hydrogen bonding shown in the image below
As you have already figured out, diethyl ether is a small dipole due to the electronegativity difference between carbon and oxygen, which can also be seen in this electron density plot. As both dipole moment vectors point roughly in the same direction, they do not cancel each other out like in the case of carbon dioxide, so the molecule has a net dipole moment and is therefore (weakly) polar.
London dispersion forces, which result from short-lived dipoles induced by fluctuations in the electron shell of molecules, are also present. They are responsible for the weak interactions between the alkyl chains, like in other alkanes and non-polar molecules. The permanent dipoles can also interact with each other, in the form of intermolecular attractive interactions between centers with $\delta+$ and $\delta-$ partial charge (and likewise repulsion between centers of equal partial charge).
Hydrogen bonding between C-H groups and oxygens, although possible in principle (see comments to your question) and, for example, found in protein structures, can be neglected in this case due to the low number of donors and the weakness of the interaction (< 17 kJ/mol). Nevertheless, the ether oxygen can act as a hydrogen bond acceptor in combination with better hydrogen bond donors like OH groups, which explains why diethyl ether is sparingly soluble in water despite its low polarity (69 g/l at 20 °C (source)). On the other hand, the absence of hydrogen bonding between ether molecules becomes apparent in the much lower boiling point of diethyl ether (34.6 °C, source) compared to water.
As you have already figured out, diethyl ether is a small dipole due to the electronegativity difference between carbon and oxygen, which can also be seen in this electron density plot. As both dipole moment vectors point roughly in the same direction, they do not cancel each other out like in the case of carbon dioxide, so the molecule has a net dipole moment and is therefore (weakly) polar.
London dispersion forces, which result from short-lived dipoles induced by fluctuations in the electron shell of molecules, are also present. They are responsible for the weak interactions between the alkyl chains, like in other alkanes and non-polar molecules. The permanent dipoles can also interact with each other, in the form of intermolecular attractive interactions between centers with $\delta+$ and $\delta-$ partial charge (and likewise repulsion between centers of equal partial charge).
Hydrogen bonding between C-H groups and oxygens, although possible in principle (see comments to your question) and, for example, found in protein structures, can be neglected in this case due to the low number of donors and the weakness of the interaction (< 17 kJ/mol). Nevertheless, the ether oxygen can act as a hydrogen bond acceptor in combination with better hydrogen bond donors like OH groups, which explains why diethyl ether is sparingly soluble in water despite its low polarity (69 g/l at 20 °C (source)). On the other hand, the absence of hydrogen bonding between ether molecules becomes apparent in the much lower boiling point of diethyl ether (34.6 °C, source) compared to water.
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Clarifying a portion of the answer in the "Best Answer" you cannot have hydrogen bonding with a C-H bond. You only have hydrogen bonding with F-H, O-H, and N-H bonds. The hydrogen bonding in proteins usually results from amide hydrogen bonding shown in the image below
Clarifying a portion of the answer in the "Best Answer" you cannot have hydrogen bonding with a C-H bond. You only have hydrogen bonding with F-H, O-H, and N-H bonds. The hydrogen bonding in proteins usually results from amide hydrogen bonding shown in the image below
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