Positive charge of NAD+ molecule

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The discussion centers on the positive charge of the NAD+ molecule, specifically located on the nitrogen atom in the nicotinamide group. The nitrogen typically forms four bonds, raising questions about its charge since nitrogen has three valence electrons. The confusion arises from the assumption that this would lead to a negative charge. However, when examining the Lewis dot structure, it is noted that the nitrogen has a free lone pair of electrons before being protonated by H+, which contributes to the positive charge upon protonation. The formal charge on nitrogen is determined by considering all electrons in lone pairs and half of the bonding electrons. Thus, with four bonds (accounting for four electrons) and two inner shell electrons, nitrogen effectively has six electrons compared to its seven protons, resulting in a positive charge. The discussion clarifies that protonation does not leave an anion but rather results in a positively charged species.
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Why is the positive charge of the NAD+ molecule located on the nitrogen in the nicotinamide group? This nitrogen has 4 bonds attached to it, but nitrogen only has 3 holes in its valence shell, so wouldn't this make a negative charge on this nitrogen?
 
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tickle_monste said:
Why is the positive charge of the NAD+ molecule located on the nitrogen in the nicotinamide group? This nitrogen has 4 bonds attached to it, but nitrogen only has 3 holes in its valence shell, so wouldn't this make a negative charge on this nitrogen?

Draw the lewis dot structure for the nitrogen in this system and you will see a free lone pair of electrons before protonation by H+. Is it true that when you protonate a neutral molecule with H+ you are left with an anion?
 
In general, for determining the formal charge on an atom, we consider all of the electrons in lone pairs and inner shells as belonging to that atom as well ashalf of the electrons in chemical bonds as belonging to that atom. Therefore, the nitrogen has 4 bonds attached to it (giving 4 electrons) plus two inner shell electrons, giving a total of 6 electrons to nitrogen's 7 protons.
 
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