Can =NH2+ in Arginine's side chain form hydrogen bonding at physiological pH?
I know that at physiological pH, Arginine will have its $ce{=NH}$ protonated to $ce{=NH2+}$. I was wondering if this $ce{=NH2+}$ can still form a hydrogen bond by being a donor? And does the positive charge on Nitrogen affect the hydrogen bonding's strength? My confusion stems from the definition of hydrogen bonding, which says that hydrogen's electron cloud needs to be withdrawn by a more electronegative atom like $ce{F, O, N}$ to be partially positive enough to participate. Therefore, I believe that the positively charged N will withdraw electrons from hydrogens more strongly, leading to more partially positively charged hydrogen and eventually stronger H-bonding with another molecule. Could someone please verify this for me?
Moreover, I have seen $ce{=O}$ and $ce{=N}$ forming hydrogen bonding by being an acceptor. However, I tried search but did not find any example of $ce{=NH3+}$ or $ce{=NH2R+}$ or NHR2+ forming hydrogen bonding as a donor. So can a Nitrogen with a double bond still participate in hydrogen bonding as a donor?
hydrogen-bond proteins amino-acids
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I know that at physiological pH, Arginine will have its $ce{=NH}$ protonated to $ce{=NH2+}$. I was wondering if this $ce{=NH2+}$ can still form a hydrogen bond by being a donor? And does the positive charge on Nitrogen affect the hydrogen bonding's strength? My confusion stems from the definition of hydrogen bonding, which says that hydrogen's electron cloud needs to be withdrawn by a more electronegative atom like $ce{F, O, N}$ to be partially positive enough to participate. Therefore, I believe that the positively charged N will withdraw electrons from hydrogens more strongly, leading to more partially positively charged hydrogen and eventually stronger H-bonding with another molecule. Could someone please verify this for me?
Moreover, I have seen $ce{=O}$ and $ce{=N}$ forming hydrogen bonding by being an acceptor. However, I tried search but did not find any example of $ce{=NH3+}$ or $ce{=NH2R+}$ or NHR2+ forming hydrogen bonding as a donor. So can a Nitrogen with a double bond still participate in hydrogen bonding as a donor?
hydrogen-bond proteins amino-acids
edited 1 hour ago
A.K.
8,35341961
asked 4 hours ago
EllBe EllBe
211
New contributor
EllBe is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
Welcome to Chemistry.SE! Please note that formulas can be better expressed with $ce{ }$ for chemical formulas/equations, $ $ for math term/equations, and $pu{ }$ for units. More information is available in this meta post Also, take a minute to look over the help center and tour page to better understand our guidelines and question policies if you haven't already.
– A.K.
1 hour ago
add a comment |
I know that at physiological pH, Arginine will have its $ce{=NH}$ protonated to $ce{=NH2+}$. I was wondering if this $ce{=NH2+}$ can still form a hydrogen bond by being a donor? And does the positive charge on Nitrogen affect the hydrogen bonding's strength? My confusion stems from the definition of hydrogen bonding, which says that hydrogen's electron cloud needs to be withdrawn by a more electronegative atom like $ce{F, O, N}$ to be partially positive enough to participate. Therefore, I believe that the positively charged N will withdraw electrons from hydrogens more strongly, leading to more partially positively charged hydrogen and eventually stronger H-bonding with another molecule. Could someone please verify this for me?
Moreover, I have seen $ce{=O}$ and $ce{=N}$ forming hydrogen bonding by being an acceptor. However, I tried search but did not find any example of $ce{=NH3+}$ or $ce{=NH2R+}$ or NHR2+ forming hydrogen bonding as a donor. So can a Nitrogen with a double bond still participate in hydrogen bonding as a donor?
hydrogen-bond proteins amino-acids
edited 1 hour ago
A.K.
8,35341961
asked 4 hours ago
EllBe EllBe
211
New contributor
EllBe is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
I know that at physiological pH, Arginine will have its $ce{=NH}$ protonated to $ce{=NH2+}$. I was wondering if this $ce{=NH2+}$ can still form a hydrogen bond by being a donor? And does the positive charge on Nitrogen affect the hydrogen bonding's strength? My confusion stems from the definition of hydrogen bonding, which says that hydrogen's electron cloud needs to be withdrawn by a more electronegative atom like $ce{F, O, N}$ to be partially positive enough to participate. Therefore, I believe that the positively charged N will withdraw electrons from hydrogens more strongly, leading to more partially positively charged hydrogen and eventually stronger H-bonding with another molecule. Could someone please verify this for me?
Moreover, I have seen $ce{=O}$ and $ce{=N}$ forming hydrogen bonding by being an acceptor. However, I tried search but did not find any example of $ce{=NH3+}$ or $ce{=NH2R+}$ or NHR2+ forming hydrogen bonding as a donor. So can a Nitrogen with a double bond still participate in hydrogen bonding as a donor?
hydrogen-bond proteins amino-acids
hydrogen-bond proteins amino-acids
edited 1 hour ago
A.K.
8,35341961
asked 4 hours ago
EllBe EllBe
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edited 1 hour ago
A.K.
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asked 4 hours ago
EllBe EllBe
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edited 1 hour ago
A.K.
8,35341961
edited 1 hour ago
A.K.
8,35341961
edited 1 hour ago
A.K.
8,35341961
8,35341961
asked 4 hours ago
EllBe EllBe
211
New contributor
EllBe is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
asked 4 hours ago
EllBe EllBe
211
asked 4 hours ago
EllBe EllBe
211
211
New contributor
EllBe is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
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New contributor
EllBe is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
EllBe is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
Welcome to Chemistry.SE! Please note that formulas can be better expressed with $ce{ }$ for chemical formulas/equations, $ $ for math term/equations, and $pu{ }$ for units. More information is available in this meta post Also, take a minute to look over the help center and tour page to better understand our guidelines and question policies if you haven't already.
– A.K.
1 hour ago
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Welcome to Chemistry.SE! Please note that formulas can be better expressed with $ce{ }$ for chemical formulas/equations, $ $ for math term/equations, and $pu{ }$ for units. More information is available in this meta post Also, take a minute to look over the help center and tour page to better understand our guidelines and question policies if you haven't already.
– A.K.
1 hour ago
Welcome to Chemistry.SE! Please note that formulas can be better expressed with $ce{ }$ for chemical formulas/equations, $ $ for math term/equations, and $pu{ }$ for units. More information is available in this meta post Also, take a minute to look over the help center and tour page to better understand our guidelines and question policies if you haven't already.
– A.K.
1 hour ago
Welcome to Chemistry.SE! Please note that formulas can be better expressed with $ce{ }$ for chemical formulas/equations, $ $ for math term/equations, and $pu{ }$ for units. More information is available in this meta post Also, take a minute to look over the help center and tour page to better understand our guidelines and question policies if you haven't already.
– A.K.
1 hour ago
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Yes, the arginine side chain is an excellent hydrogen bond donor. Charged N-H groups are even better hydrogen bond donors than the corresponding neutral N-H groups. Here is an article that gives examples of arginine side chains in hydrogen bonds. It showcases bidendate hydrogen bonds (i.e. two hydrogen bonds from the arginine side chain) with carboxylates and with nitrogenous bases of nucleic acids.
Specifically for proteins, if the hydrogen bond donor is positively charge (e.g. Arg+) and the hydrogen bond acceptor is negatively charged (e.g. Glu-), you have a combination of ionic and hydrogen bond interaction, which is particularly strong. It is often referred to as a salt bridge, such as in this example. If you take a close look at the arginine side chain, you will see that it is protonated (i.e. positively charged) and interacts with two negatively charged carboxylate groups.
answered 3 hours ago
Karsten TheisKarsten Theis
4799
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Yes, the arginine side chain is an excellent hydrogen bond donor. Charged N-H groups are even better hydrogen bond donors than the corresponding neutral N-H groups. Here is an article that gives examples of arginine side chains in hydrogen bonds. It showcases bidendate hydrogen bonds (i.e. two hydrogen bonds from the arginine side chain) with carboxylates and with nitrogenous bases of nucleic acids.
Specifically for proteins, if the hydrogen bond donor is positively charge (e.g. Arg+) and the hydrogen bond acceptor is negatively charged (e.g. Glu-), you have a combination of ionic and hydrogen bond interaction, which is particularly strong. It is often referred to as a salt bridge, such as in this example. If you take a close look at the arginine side chain, you will see that it is protonated (i.e. positively charged) and interacts with two negatively charged carboxylate groups.
answered 3 hours ago
Karsten TheisKarsten Theis
4799
add a comment |
Yes, the arginine side chain is an excellent hydrogen bond donor. Charged N-H groups are even better hydrogen bond donors than the corresponding neutral N-H groups. Here is an article that gives examples of arginine side chains in hydrogen bonds. It showcases bidendate hydrogen bonds (i.e. two hydrogen bonds from the arginine side chain) with carboxylates and with nitrogenous bases of nucleic acids.
Specifically for proteins, if the hydrogen bond donor is positively charge (e.g. Arg+) and the hydrogen bond acceptor is negatively charged (e.g. Glu-), you have a combination of ionic and hydrogen bond interaction, which is particularly strong. It is often referred to as a salt bridge, such as in this example. If you take a close look at the arginine side chain, you will see that it is protonated (i.e. positively charged) and interacts with two negatively charged carboxylate groups.
answered 3 hours ago
Karsten TheisKarsten Theis
4799
add a comment |
Yes, the arginine side chain is an excellent hydrogen bond donor. Charged N-H groups are even better hydrogen bond donors than the corresponding neutral N-H groups. Here is an article that gives examples of arginine side chains in hydrogen bonds. It showcases bidendate hydrogen bonds (i.e. two hydrogen bonds from the arginine side chain) with carboxylates and with nitrogenous bases of nucleic acids.
Specifically for proteins, if the hydrogen bond donor is positively charge (e.g. Arg+) and the hydrogen bond acceptor is negatively charged (e.g. Glu-), you have a combination of ionic and hydrogen bond interaction, which is particularly strong. It is often referred to as a salt bridge, such as in this example. If you take a close look at the arginine side chain, you will see that it is protonated (i.e. positively charged) and interacts with two negatively charged carboxylate groups.
answered 3 hours ago
Karsten TheisKarsten Theis
4799
Yes, the arginine side chain is an excellent hydrogen bond donor. Charged N-H groups are even better hydrogen bond donors than the corresponding neutral N-H groups. Here is an article that gives examples of arginine side chains in hydrogen bonds. It showcases bidendate hydrogen bonds (i.e. two hydrogen bonds from the arginine side chain) with carboxylates and with nitrogenous bases of nucleic acids.
Specifically for proteins, if the hydrogen bond donor is positively charge (e.g. Arg+) and the hydrogen bond acceptor is negatively charged (e.g. Glu-), you have a combination of ionic and hydrogen bond interaction, which is particularly strong. It is often referred to as a salt bridge, such as in this example. If you take a close look at the arginine side chain, you will see that it is protonated (i.e. positively charged) and interacts with two negatively charged carboxylate groups.
answered 3 hours ago
Karsten TheisKarsten Theis
4799
edited 3 hours ago
answered 3 hours ago
Karsten TheisKarsten Theis
4799
answered 3 hours ago
Karsten TheisKarsten Theis
4799
answered 3 hours ago
Karsten TheisKarsten Theis
4799
4799
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Welcome to Chemistry.SE! Please note that formulas can be better expressed with $ce{ }$ for chemical formulas/equations, $ $ for math term/equations, and $pu{ }$ for units. More information is available in this meta post Also, take a minute to look over the help center and tour page to better understand our guidelines and question policies if you haven't already.
– A.K.
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