NH2COOH Lewis Structure & Characteristics (15 Helpful Facts)

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NH2COOH or carbamic acid is an aminocarboxylic acid formed by NH3 and CO2. Let us discuss various aspects of the organic compound in this article.

NH2COOH or carbamic acid involves the combination of 2 organic functionalities which are amide and carboxylate. It is formed by the sharing of electrons between the amide nitrogen and carboxylate carbon by a single covalent bond thereby completing the octet.

NH2COOH is a significant compound in peptide and protein synthesis. Industrially it is used in urea production and as a muscle relaxant. In various organic reactions, it is used to protect the amine. Let us explore its bonding and physical properties like solubility, hybridization, polarity, etc.

How to draw the NH2COOH lewis structure?

NH2COOH lewis structure can be best represented by electron dot symbols. Let us draw it sequentially.

Total no. of valence electrons involved

The very first step is to find out the no. of electrons involved in bonding. In the NH2COOH lewis structure, the total no. of valence electrons is 24. It is calculated by the addition of the individual valence electrons in N, H, C, and O.

Looking out for the central atom

The next step is to check out the central atom which is of the least electronegativity. Keeping the criteria, then in NH2COOH O is most electronegative and H is least electronegative, but it cannot be the preferred choice due to the small atomic radius. Hence the whole structure will assemble around N and C due to planarity.

Fulfilling the octet

Octet criteria in NH2COOH lewis structure are completed by sharing of electrons. N shares its electrons with 2H and C by single covalent bonds. Similarly, C shares its electrons with O and OH by double and single covalent bonds respectively thereby completing the criteria.

The formal charge for stability

Calculation of the formal charge of the individual atoms in NH2COOH can confirm the existence of the molecule. Here the formal charge of all the individual atoms is 0 which points towards equal electric field distribution in the molecule.

NH2COOH lewis structure
Carbamic acid NH2COOH representation

NH2COOH lewis structure shape

The shape of any organic molecule explains the arrangement of individual atoms. Let us discuss shape in NH2COOH.

NH2COOH has a planar shape where amide and carboxyl groups are joined by a single covalent bond responsible for its planarity. Unlike many amide compounds, the H2N group of NH2COOH is not protonated which again confirms the planar shape.

NH2Cooh
NH2COOH 3D planar shape

NH2COOH lewis structure formal charge

The formal charge is the equal electric distribution of individual atoms around the molecule. Let us calculate the formal charge of NH2COOH.

The formal charge of NH2COOH is 0. It can be computed by the formula, Formal charge = No. of valence electrons – No. of nonbonding electrons – Bonding electrons/2

  • Formal charge of N in NH2COOH = 5 – 2 – 6/2 = 0
  • Formal charge of C in NH2COOH = 4 – 0 – 8/2 = 0
  • Formal charge of O in NH2COOH = 6 – 2 – 4/2 = 0
  • Formal charge of O (OH) in NH2COOH = 6 – 4 – 4/2 = 0
  • Hence the formal charge of NH2COOH is 0.

NH2COOH lewis structure angle

NH2COOH is a complex organic molecule because of its planarity and its bond angles can vary. Let us throw light on the same.

NH2COOH has a bond angle of 120 around the central carbonyl group because of its planarity. The lone pair around N shows conjugation which is responsible for 120 degrees around the N atom as well.

NH2COOH lewis structure octet rule

Octet rule criteria are followed by main group elements by sharing or transference of electrons. Let us check out the octet rule in the NH2COOH.

NH2COOH follows the octet rule by sharing electrons. There are 2 main components NH2 and COOH which are joined by a single covalent bond. N forms 3 single covalent bonds and C forms 2 single and 1 double covalent bond thereby fulfilling the criteria.

NH2COOH lewis structure lone pairs

Lone pairs do not have a role in bonding but influence the arrangements caused by repulsions. Let us find out the lone pair in the NH2COOH.

NH2COOH has a single lone pair of electrons that are present on the N atom. N has 5 valence electrons where 2 are shared by the hydrogen atoms and the 3rd one is shared with the carboxyl group. The lone pair around N is also responsible for conjugation.

NH2COOH valence electrons

Valence electrons due to less nuclear attractiveness are more prone to bonding. Let us discuss the no. of valence electrons involved in bonding.

The total no. of valence electrons in NH2COOH is 24. It can be calculated by the addition of the individual atoms N, H, C, and O.

  • Valence electrons in N in NH2COOH = 5
  • Valence electrons in H in NH2COOH = 1
  • Valence electrons in C in NH2COOH = 4
  • Valence electrons in O in NH2COOH = 6
  • Total no. of valence electrons in NH2COOH = 5 + 3(1) + 4 + 2(6) = 24

NH2COOH hybridization

Hybridization is the intermixing of the atomic orbitals in organic compounds which results in the formation of hybrid orbitals. Let us find out the hybridization in NH2COOH.

The hybridization of NH2COOH around the C atom is sp2 because it is a planar structure. Also, N is in conjugation with the C atom due to the presence of lone pair which implies that around N also hybridization is sp2.

Is NH2COOH solid or liquid?

The state of matter of a compound can be judged by the reaction and preparation conditions of the compound. Let us find out the same in NH2COOH.

NH2COOH is a solid because it is prepared by the reaction of two gases NH3 and CO2 at very low temperatures which results in the solidification of the product. Its existence as the dimers of hydrogen bonding is an indicator of its strong interactions which confirms its solid nature.

Is NH2COOH soluble in water?

Solubility is the ability of compounds to dissolve in various mediums. Let us check out the solubility of NH2COOH in water.

NH2COOH is soluble in water because of its weak acidity. Carboxylate is a large organic functional group with high molecular weight, and it is difficult for it to dissolve in water. But because of its weak acidity and absence of a carbon chain its solubility in water increases.

Is NH2COOH polar or nonpolar?

The polarity of the molecule depends on the electric field charge distribution and the shape. Let us figure out polarity in NH2COOH.

NH2COOH is a semi-polar compound as it has differences in the electric charge distribution and have a net dipole moment. But the difference in the charges is not much pronounced as the atoms involved can be donors and acceptors with various interactions at O and N termini.

Is NH2COOH a molecular compound?

Molecular compounds are synonymous with covalent compounds in terms of properties. Let us discuss molecularity in NH2COOH

NH2COOH is a molecular compound because here the individual atoms are linked together by sharing of electrons. It is an organic compound that belongs to the carbonic acid functionalities and is synthesized enzymatically by urea which are indicators of its molecularity.

Is NH2COOH acid or base?

Acidic or basic character depends on the substituents attached to the molecule. Let us discuss the same in NH2COOH.

NH2COOH is an acid more specifically amino acid because of the presence of a weak carboxylate group attached to the amide nitrogen. It is considered a weak acid because of its partial dissociation capacity as compared to inorganic acids.

Is NH2COOH electrolyte?

Electrolytic property is dependent on the dissociation capacity of the compound in the aqueous medium. Let us check out the same in NH2COOH.

NH2COOH is not an electrolyte because it is an organic compound. Despite being soluble in water it is not able to fully dissociate in water. Instead, it is partially dissociated and is not able to facilitate the movement of ions.

Is NH2COOH salt?

Salt determination of any compound is dependent on the neutralization reaction. Let us discuss whether NH2COOH is a salt or not.

NH2COOH is not salt because it has an organic acid functionality in it. The acidic organic functionality is carboxylate or COOH group. Though weak as compared to inorganic acid, it is named carbamic acid and is designated as an amino acid.

Is NH2COOH ionic or covalent?

The nature of any compound is judged by its bonding and its electronic behavior in compound formation. Let us check out the same in NH2COOH.

NH2COOH is a covalent compound because here there is sharing of electrons. All the individual atoms are bound together by both single and double covalent bonds. Also, it is an organic compound involving nonmetal entities confirming its covalency.

Conclusion

In nutshell, NH2COOH is an organic amino acid of class carbamate and like many other organic compounds, it exhibits bonding properties and physical properties. But because of the involvement of both amide and carboxylate groups, it shows anomalous behavior in acid-base character and polarity.

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