hybridization

[coolchix321]

What is the hybridization of NR3 (amine)? sp3? How do you get that?
What about for an amide? What is it's hybridization?
How?

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[injunjoe]

NR3 (non-ionic state) should be tetrahedral...3 alkyl substituents and 1 lone pair

 

[maverick09]

injungoe is correct. NR3 is sp3 hybridized. in regards to your question about amides, there's an exception to rule. for the nitrogen adjacent to an sp2 carbon (in this case, the carbonyl carbon) it is also sp2 due to resonance--it must have a lone pair of course. this is why peptide bonds are planar and thus don't rotate making our proteins very stable structures.

 

[injunjoe]

injungoe is correct. NR3 is sp3 hybridized. in regards to your question about amides, there's an exception to rule. for the nitrogen adjacent to an sp2 carbon (in this case, the carbonyl carbon) it is also sp2 due to resonance. this is why peptide bonds are planar and thus don't rotate making our proteins very stable structures.

injungoe?!injungoe?!! who the hell is that haha

 

[coolchix321]

What is the hybridization of NR3 (amine)? How do you get that?
Why are amides sp2? i still dont understand
thanks

injungoe is correct. NR3 is sp3 hybridized. in regards to your question about amides, there's an exception to rule. for the nitrogen adjacent to an sp2 carbon (in this case, the carbonyl carbon) it is also sp2 due to resonance--it must have a lone pair of course. this is why peptide bonds are planar and thus don't rotate making our proteins very stable structures.

 

[maverick09]

NR3 (amine) is sp3 hybridized. i got this by counting the number of attached atoms + the number of loan pairs. NR3 has one loan pair and 3 R-groups.

the nitrogen in an amide (assuming the nitrogen has a loan pair on it) is sp2 hybridized. this is an exception to the rule that they love to test on the mcat.

here's the short version to memorize: if a nitrogen atom (with a loan pair) is adjacent to an sp2 carbon, THEN the nitrogen is also sp2

here's the reason: through resonance, the nitrogen can form a double bond with the carbonyl carbon in an amide (thus kicking up the double bond between carbon and oxygen and giving oxygen a negative charge and nitrogen a positive charge).

hope that helps