Preheat the oven to 375 degrees F (190 degrees C). Line 2 baking sheets with parchment paper.
Beat together 1 1/2 cups sugar, butter, vanilla, and salt in a large bowl with an electric mixer until light and fluffy. Beat in eggs one at a time, mixing well after each addition. Mix in cream of tartar and baking soda. Beat in cocoa powder, 1/2 teaspoon cinnamon, and cayenne powder. Beat in flour. Stir chocolate chips into dough until incorporated.
Mix together remaining 1/4 cup sugar and 1/2 teaspoon cinnamon in a small bowl.
Roll heaping tablespoons of dough into balls. Roll balls in sugar-cinnamon mixture and place 2 inches apart onto the prepared baking sheets.
Bake in the preheated oven until centers are set and edges are slightly cracked, about 10 minutes. Cool on the baking sheets for about 5 minutes before removing to a wire rack to cool completely.